Thiourea → Ethyl 2-methoxyimino-2-(2-aminothiazol-4-yl)acetate hydrobromide

HRID 1155157Notes

Reaction equation

HRID 1155157 reaction equation
[CH3:1][O:2][N:3]=[C:4]([C:10]([CH2:12][Br:13])=O)[C:5]([O:7][CH2:8][CH3:9])=[O:6].[NH2:14][C:15]([NH2:17])=[S:16]>C(O)C>[BrH:13].[CH3:1][O:2][N:3]=[C:4]([C:10]1[N:14]=[C:15]([NH2:17])[S:16][CH:12]=1)[C:5]([O:7][CH2:8][CH3:9])=[O:6]

Participants

4

Reactant 2

HCID 2723790ThioureaHCID 54053279Butanoic acid, 4-bromo-2-(methoxyimino)-3-oxo-, ethyl ester

Product 1

HCID 73668749Ethyl 2-methoxyimino-2-(2-aminothiazol-4-yl)acetate hydrobromide

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of ethyl 2-methoxyimino-4-bromoacetoacetate (a mixture of syn and anti isomers) (17.4 g.) and thiourea (5.4 g.) in ethanol (100 ml.) was refluxed for 4 hours. The reaction mixture was allowed to stand in a refrigerator to precipitate crystals. The crystals were collected by filtration, washed with ethanol and dried to give ethyl 2-methoxyimino-2-(2-aminothiazol-4-yl)acetate hydrobromide (anti isomer) (9.5 g.). The filtrate and the washings were put together and concentrated under reduced pressure. Water (100 ml.) was added to the residue and the mixture was washed with ether.

Workup

  1. temperaturewas refluxed for 4 hours
  2. customto precipitate crystals
  3. filtrationThe crystals were collected by filtration
  4. washwashed with ethanol
  5. customdried

Sources & evidence

ORD record
ord-6d636eafaf48447bb21a71ac6646d0c3
Source dataset
uspto-grants-1981_11
Patent number
US04299829

Reaction notes

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