US5428172A
Expired / Lapsed
US
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Preparation of 3-dihaloacetyl oxazolidines
Assignee: Monsanto Technology LLC
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Filing: 1993-09-21
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Granted: 1995-06-27
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Expires: 2013-09-21
Abstract
Abstract The disclosure herein relates to a new process for the preparation of 3-dihaloacetyl (un)substituted oxazolidine compounds by the catalytic hydrogenation of nitroalcohols with aldehydes or ketones followed by reaction with a dihaloacetyl halide.
Inventors
- 👤 William D. Taylor
- 👤 Bruce J. Gaede
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-31 17:35
CPC Classifications
C; C07; C07D; C07D263/00; C07D263/02; C07D263/04; C07D413/00; C07D413/02; C07D413/04
Claims Analysis
Total Claims: 11
Claim 1
Independent Claim
131 words
Process for preparation of compounds according to Formula A ##STR2## consisting essentially of reacting a nitroalcohol of the formula ##STR3## with a ketone having the formula ##STR4## in the presence of hydrogen and a hydrogenation catalyst at temperatures within range of 10°-80° C. and hydrogen pressures within the range of about 0.068 to 73 kg/cm 2 wherein R, R 1 and R 2 are independently H, C 1-6 alkyl, haloalkyl, alkylol or alkoxy or alkoxyalkyl having up to 8 carbon atoms; R 3 is H, or a C 1-6 alkyl, phenyl, benzyl, furanyl, thienyl, or pyridyl radical and R 4 and R 5 are independently a C 1-6 alkyl, haloalkyl, alkylol, alkoxy or alkoxyalkyl radical having up to 8 carbon atoms; provided the alkyl portion of said radicals is linear alkyl.
Claim 2
Dependent Claim
131 words
Process for preparation of compounds according to Formula A ##STR2## consisting essentially of reacting a nitroalcohol of the formula ##STR3## with a ketone having the formula ##STR4## in the presence of hydrogen and a hydrogenation catalyst at temperatures within range of 10°-80° C. and hydrogen pressures within the range of about 0.068 to 73 kg/cm 2 wherein R, R 1 and R 2 are independently H, C 1-6 alkyl, haloalkyl, alkylol or alkoxy or alkoxyalkyl having up to 8 carbon atoms; R 3 is H, or a C 1-6 alkyl, phenyl, benzyl, furanyl, thienyl, or pyridyl radical and R 4 and R 5 are independently a C 1-6 alkyl, haloalkyl, alkylol, alkoxy or alkoxyalkyl radical having up to 8 carbon atoms; provided the alkyl portion of said radicals is linear alkyl.
Claim 3
Dependent Claim
31 words
Process according to claim 1 wherein said nitroalcohol is introduced into a reaction zone in an initial incremental amount and allowed to react prior to adding the remaining charge of nitroalcohol.
Claim 4
Dependent Claim
37 words
Process according to claim 2 wherein R, R 1 and R 2 are hydrogen, R 3 is said furanyl, thienyl or pyridyl radical and R 4 and R 5 are independently H, C 1-4 alkyl or haloalkyl.
Claim 5
Dependent Claim
13 words
Process according to claim 3 wherein the compound of Formula A is 2,2-dimethyl-5-(2-furanyl)oxazolidine.
Claim 6
Dependent Claim
13 words
Process according to claim 3 wherein the compound of Formula A is 2,2-dimethyl-5-(2-thienyl)oxazolidine.
Claim 7
Dependent Claim
13 words
Process according to claim 3 wherein the compound of Formula A is 2,2-dimethyl-5-(3-pyridyl)oxazolidine.
Claim 8
Dependent Claim
47 words
Process according to claim 1 wherein said compound of Formula A is further reacted with a dihaloacetyl halide compound to form the corresponding 3-dihaloacetyl-(un)substituted oxazolidine according to Formula B. ##STR5## wherein R and R 1 -R 5 are as defined in claim 1 and X is halogen.
Claim 9
Dependent Claim
14 words
Process according to claim 7 wherein the halogen group in Formula B is chlorine.
Claim 10
Dependent Claim
24 words
Process according to claim 8 wherein the compound of Formula B is the 3-dichloroacetyl oxazolidine of a compound according to any of claims 5-7.
Claim 11
Dependent Claim
13 words
Process according to claim 9 wherein said compound of Formula B is 3-dichloroacetyl-2,2-dimethyl-5-(2-furanyl)oxazolidine.
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USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1998-06-26 | 1998-12-26 | 1999-06-27 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 2002-06-26 | 2002-12-26 | 2003-06-27 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 2006-06-26 | 2006-12-26 | 2007-06-27 | $7700.00 | Window Closed / Lapsed |