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US4086274A
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N-(2-mercapto-ethyl)alkanamides from H2 S and 2-H-2-oxazolines or 2-alkyl-2-oxazolines
Assignee: Dow Chemical Co
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Filing: 1976-11-22
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Granted: 1978-04-25
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Expires: 1996-11-22
Abstract
Abstract N-(2-mercaptoethyl)alkanamides are produced by reacting hydrogen sulfide with 2-H-2-oxazolines or 2-alkyl-2-oxazolines. For example, N-(2-mercaptoethyl)acetamide was prepared in excellent yields by incrementally adding 2-methyl-2-oxazoline to a stirred solution of hydrogen sulfide in methanol under autogeneous pressure at about 100° C.
Inventors
- 👤 Mark E. Kaiser
- 👤 Peter W. Owen
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-08 04:47
CPC Classifications
C; C07; C07C; C07C231/00; C07C233/00; C07C233/01; C07C233/16
Claims Analysis
Total Claims: 16
Claim 1
Independent Claim
51 words
A process of preparing a N-(2-mercaptoethyl)alkanamide comprising reacting by contacting under essentially anhydrous conditions (a) a 2-H-2-oxazoline or a 2-alkyl-2-oxazoline of the formula: ##STR2## in which R is hydrogen or alkyl and R 1 -R 4 are each independently hydrogen, lower alkyl, hydroxy-substituted lower alkyl or phenyl, with (b) hydrogen sulfide.
Claim 2
Dependent Claim
51 words
A process of preparing a N-(2-mercaptoethyl)alkanamide comprising reacting by contacting under essentially anhydrous conditions (a) a 2-H-2-oxazoline or a 2-alkyl-2-oxazoline of the formula: ##STR2## in which R is hydrogen or alkyl and R 1 -R 4 are each independently hydrogen, lower alkyl, hydroxy-substituted lower alkyl or phenyl, with (b) hydrogen sulfide.
Claim 3
Dependent Claim
17 words
The process defined by claim 1 in which the molar ratio of (b):(a) is at least 1.
Claim 4
Dependent Claim
17 words
The process defined by claim 1 in which the reaction is conducted in an inert organic solvent.
Claim 5
Dependent Claim
23 words
The process defined by claim 3 in which the inert organic solvent is a lower alkanol of from 1 to 4 carbon atoms.
Claim 6
Dependent Claim
14 words
The process defined by claim 4 in which the inert organic solvent is methanol.
Claim 7
Dependent Claim
13 words
The process defined by claim 1 in which the reaction is conducted neat.
Claim 8
Dependent Claim
19 words
The process defined by claim 1 in which R is alkyl of from 1 to about 18 carbon atoms.
Claim 9
Dependent Claim
29 words
The process defined by claim 7 in which R 1 and R 2 are hydrogen, methyl, ethyl or hydroxy methyl and R 3 and R 4 are each hydrogen.
Claim 10
Dependent Claim
21 words
The process defined by claim 8 in which R 1 -R 4 are each hydrogen and R is methyl or ethyl.
Claim 11
Dependent Claim
23 words
The process defined by claim 1 in which the reaction is conducted at a temperature of from about 20° to about 200° C.
Claim 12
Dependent Claim
19 words
The process defined by claim 10 in which the reaction temperature is from about 50° to about 150° C.
Claim 13
Dependent Claim
18 words
The process defined by claim 1 in which the process is conducted neat under autogenous or superatmospheric pressure.
Claim 14
Dependent Claim
40 words
The process defined by claim 2 wherein (a) is 2-methyl-2-oxazoline or 2-ethyl-2-oxazoline and wherein the reaction is conducted neat or in a methanol solution at a temperature of from about 50° to about 150° C under autogenous or superatmospheric pressure.
Claim 15
Dependent Claim
11 words
The process defined by claim 1 in which R is hydrogen.
Claim 16
Dependent Claim
25 words
The process defined by claim 1 which comprises the additional step of hydrolyzing the N-(2-mercaptoethyl)alkanamide with an aqueous protic acid to thereby form a 2-mercaptoethylamine.
References Cited (Backward Citations)
US3414620A
Cited
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1981-04-24 | 1981-10-24 | 1982-04-25 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1985-04-24 | 1985-10-24 | 1986-04-25 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1989-04-24 | 1989-10-24 | 1990-04-25 | $7700.00 | Window Closed / Lapsed |