GB698561A - Process for the preparation of technically valuable oxazolines - Google Patents
Process for the preparation of technically valuable oxazolinesInfo
- Publication number
- GB698561A GB698561A GB3414/51A GB341451A GB698561A GB 698561 A GB698561 A GB 698561A GB 3414/51 A GB3414/51 A GB 3414/51A GB 341451 A GB341451 A GB 341451A GB 698561 A GB698561 A GB 698561A
- Authority
- GB
- United Kingdom
- Prior art keywords
- threo
- nitrophenyl
- dichloracetamido
- preparation
- oxazoline
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired
Links
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D263/00—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings
- C07D263/02—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings
- C07D263/08—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
- C07D263/10—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
- C07D263/14—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms with radicals substituted by oxygen atoms
Abstract
The threo forms of 2-dichloromethyl-4-hydroxymethyl - 5 - p - nitrophenyl - D 2 - oxazoline are manufactured by treating a readily hydrolysable carboxylic acid ester of a threo 2 - dichloracetamido - 1 - p - nitrophenyl - 1 - chloro-3-hydroxypropane with a dilute aqueous solution of an alkali metal (e.g. sodium or potassium) hydroxide, thereby effecting both cyclization and hydrolysis of the acyloxy group. The process is advantageously effected at a temperature not substantially in excess of room temperature, in the presence of a water-miscible inert organic solvent, and may be combined with the preparation of the starting materials by mono-esterifying an erythro 2-dichloracetamido - 1 - p - nitrophenylpropane - 1 : 3 - diol in the 3-position and treating the product with thionyl chloride. The process is applicable particularly to the preparation of the DL- and D-threo forms of the oxazoline, which possess antibiotic activity and are also useful as intermediates for the preparation of chloramphenicol and the racemate of which it is the D-component. Examples describe the action of aqueous ethanolic caustic soda on DL- and D-threo 2 - dichloroacetamido - 1 - p - nitrophenyl-1-chloro-3-acetoxypropane, on the acid succinate of DL-threo 2-dichloracetamido-1-p-nitrophenyl - 1 - chloropropane - 3 - ol, and on DL - threo - 2 - dichloracetamido - 1 - p - nitrophenyl - 3 - carbethoxyoxypropane. Specifications 698,544 and 698,562 are referred to. Reference has been directed by the Comptroller to Specification 698,542.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR698561X | 1950-07-21 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB698561A true GB698561A (en) | 1953-10-21 |
Family
ID=9047752
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB3414/51A Expired GB698561A (en) | 1950-07-21 | 1951-02-12 | Process for the preparation of technically valuable oxazolines |
Country Status (1)
| Country | Link |
|---|---|
| GB (1) | GB698561A (en) |
-
1951
- 1951-02-12 GB GB3414/51A patent/GB698561A/en not_active Expired
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