Benzene → Ethyl 2-hydroxyimino-2-(2-methyl-1,3-thiazol-4-yl)acetate

HRID 1447271Notes

Reaction equation

HRID 1447271 reaction equation
[OH:1][N:2]=[C:3]([C:9]([CH2:11]Br)=O)[C:4]([O:6][CH2:7][CH3:8])=[O:5].[C:13]([NH2:16])(=[S:15])[CH3:14].C1C=CC=CC=1>C(N(CC)CC)C>[OH:1][N:2]=[C:3]([C:9]1[N:16]=[C:13]([CH3:14])[S:15][CH:11]=1)[C:4]([O:6][CH2:7][CH3:8])=[O:5]

Participants

5

Reactant 3

HCID 241BenzeneHCID 2723949ThioacetamideHCID 178472904HCID 178472904, compound

Product 1

HCID 73178131Ethyl 2-hydroxyimino-2-(2-methyl-1,3-thiazol-4-yl)acetate

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Procedure

A mixture of ethyl 2-hydroxyimino-4-bromoacetoacetate (a mixture of syn and anti isomers) (22.0 g.), thioacetamide (7.5 g.) and benzene (100 ml.) was refluxed for 3 hours. After cooling triethylamine (10 g.) was added thereto and the mixture was stirred for 1 hour. An insoluble material was filtered off and the filtrate was concentrated under reduced pressure to give ethyl 2-hydroxyimino-2-(2-methyl-1,3-thiazol-4-yl)acetate (a mixture of syn and anti isomers) (8.6 g.). This substance was subjected to column chromatography on silica gel (80 g.) using benzene as developing solvent. Firstly the eluate containing anti isomer was eluted, collected and concentrated to give ethyl 2-hydroxyimino-2-(2-methyl-1,3-thiazol-4-yl)acetate (anti isomer) (2.5 g.), mp 90° to 92° C.

Workup

  1. temperaturewas refluxed for 3 hours
  2. additionwas added
  3. filtrationAn insoluble material was filtered off
  4. concentrationthe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-4311b4cae3f744bbaa31dccb43b25789
Source dataset
uspto-grants-1982_02
Patent number
US04316019

Reaction notes

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