US4038284A
Expired / Lapsed
US
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N-acylation of oxazolidines
Assignee: Zeneca Inc
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Filing: 1976-01-07
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Granted: 1977-07-26
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Expires: 1996-01-07
Abstract
Abstract N-substituted oxazolidines having the formula ##STR1## in which R is C 1 -C 10 haloalkyl, C 1 -C 10 alkyl or lower alkylthio; and R 1 and R 2 are independently hydrogen, C 1 -C 12 alkyl, lower alkoxyalkyl or lower alkylol; and R 3 , R 4 , R 5 and R 6 are independently hydrogen, lower alkyl, lower alkoxyalkyl or lower alkylol are prepared by reacting an oxazolidine with an acid chloride or analogous compound in the presence of a hydrogen chloride acceptor and water. The process is characterized by minimization of by-product formation. In a preferred embodiment, the oxazolidine is prepared by reaction of an alkanolamine with an aldehyde or ketone and the water of reaction is retained in the system.
Inventors
- 👤 Harold M. Pitt
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-01 10:08
CPC Classifications
C; C07; C07D; C07D263/00; C07D263/02; C07D263/04; C07D263/06
Claims Analysis
Total Claims: 16
Claim 1
Independent Claim
103 words
A process for the production of N-substituted oxazolidines having the formula ##STR12## in which R is C 1 -C 10 haloalkyl, C 1 -C 10 alkyl or lower alkylthio, R 1 and R 2 are independently hydrogen, C 1 -C 12 alkyl, lower alkoxyalkyl or lower alkylol, and R 3 , R 4 , R 5 and R 6 are independently hydrogen, lower alkyl, lower alkoxyalkyl or lower alkylol, comprising the step of reacting an oxazolidine having the formula ##STR13## with a compound having the formula ##STR14## in which X is a halogen, in the presence of an alkali metal hydroxide and water.
Claim 2
Dependent Claim
103 words
A process for the production of N-substituted oxazolidines having the formula ##STR12## in which R is C 1 -C 10 haloalkyl, C 1 -C 10 alkyl or lower alkylthio, R 1 and R 2 are independently hydrogen, C 1 -C 12 alkyl, lower alkoxyalkyl or lower alkylol, and R 3 , R 4 , R 5 and R 6 are independently hydrogen, lower alkyl, lower alkoxyalkyl or lower alkylol, comprising the step of reacting an oxazolidine having the formula ##STR13## with a compound having the formula ##STR14## in which X is a halogen, in the presence of an alkali metal hydroxide and water.
Claim 3
Dependent Claim
18 words
A process according to claim 1 in which the temperature is between about -5° and about +5° C.
Claim 4
Dependent Claim
15 words
A process according to claim 1 in which the N-substituted oxazolidine is 2,2-dimethyl-3-dichloroacetyl, 5-n-propyl oxazolidine.
Claim 5
Dependent Claim
15 words
A process according to claim 3 in which the alkali metal hydroxide is sodium hydroxide.
Claim 6
Dependent Claim
14 words
A process according to claim 1 in which the N-substituted oxazolidine is 2,2-dimethyl-3-dichloroacetyl oxazolidine.
Claim 7
Dependent Claim
14 words
A process according to claim 1 in which the N-substituted oxazolidine is 2,2,5-trimethyl-3-dichloroacetyl oxazolidine.
Claim 8
Dependent Claim
143 words
A process for the production of N-substituted oxazolidines having the formula ##STR15## in which R is C 1 -C 10 haloalkyl, C 1 -C 10 alkyl or lower alkylthio, R 1 and R 2 are independently hydrogen, C 1 -C 12 alkyl, lower alkoxyalkyl or lower alkylol, and R 3 , R 4 , R 5 and R 6 are independently hydrogen, lower alkyl, lower alkoxyalkyl or lower alkylol comprising the steps of: a. reacting an alkanolamine having the formula ##STR16## with a carbonyl compound having the formula ##STR17## to produce water and a reaction product comprising an oxazolidine; b. retaining the water in contact with the reaction product of (a); and, c. reacting the reaction product of (a), in the presence of the water and an alkali metal hydroxide, with a compound having the formula ##STR18## in which X is a halogen.
Claim 9
Dependent Claim
143 words
A process for the production of N-substituted oxazolidines having the formula ##STR15## in which R is C 1 -C 10 haloalkyl, C 1 -C 10 alkyl or lower alkylthio, R 1 and R 2 are independently hydrogen, C 1 -C 12 alkyl, lower alkoxyalkyl or lower alkylol, and R 3 , R 4 , R 5 and R 6 are independently hydrogen, lower alkyl, lower alkoxyalkyl or lower alkylol comprising the steps of: a. reacting an alkanolamine having the formula ##STR16## with a carbonyl compound having the formula ##STR17## to produce water and a reaction product comprising an oxazolidine; b. retaining the water in contact with the reaction product of (a); and, c. reacting the reaction product of (a), in the presence of the water and an alkali metal hydroxide, with a compound having the formula ##STR18## in which X is a halogen.
Claim 10
Dependent Claim
19 words
A process according to claim 7 further comprising (d) recovering the N-substituted oxazolidine from the product of step (c).
Claim 11
Dependent Claim
23 words
A process according to claim 8 in which step (c) is conducted at a temperature of between about -5 and about +5° C.
Claim 12
Dependent Claim
15 words
A process according to claim 7 in which the N-substituted oxazolidine is 2,2-dimethyl,3-dichloroacetyl, 5-n-propyl oxazolidine.
Claim 13
Dependent Claim
15 words
A process according to claim 7 in which the alkali metal hydroxide is sodium hydroxide.
Claim 14
Dependent Claim
26 words
A process according to claim 7 in which an aqueous solution of an alkali metal hydroxide is added to the system prior to conducting step (c).
Claim 15
Dependent Claim
15 words
A process according to claim 7 in which the N-substituted oxazolidine is 2,2-dimethyl, 3-dichloroacetyl oxazolidine.
Claim 16
Dependent Claim
14 words
A process according to claim 7 in which the N-substituted oxazolidine is 2,2,5-trimethyl,3-dichloroacetyl oxazolidine.
References Cited (Backward Citations)
US3707541A
Cited
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1980-07-25 | 1981-01-24 | 1981-07-26 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1984-07-25 | 1985-01-24 | 1985-07-26 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1988-07-25 | 1989-01-24 | 1989-07-26 | $7700.00 | Window Closed / Lapsed |