Water → Ethyl 2-(2-amino-4-thiazolyl)-2-propoxyiminoacetate

HRID 434624Notes

Reaction equation

HRID 434624 reaction equation
Br[CH2:2][C:3](=O)[C:4](=[N:10][O:11][CH2:12][CH2:13][CH3:14])[C:5]([O:7][CH2:8][CH3:9])=[O:6].[NH2:16][C:17]([NH2:19])=[S:18].O>C(O)C>[NH2:19][C:17]1[S:18][CH:2]=[C:3]([C:4](=[N:10][O:11][CH2:12][CH2:13][CH3:14])[C:5]([O:7][CH2:8][CH3:9])=[O:6])[N:16]=1

Participants

5

Reactant 3

HCID 962WaterHCID 2723790ThioureaHCID 54177753Ethyl 4-bromo-2-propoxyimino-acetoacetate

Product 1

HCID 53867037Ethyl 2-(2-amino-4-thiazolyl)-2-propoxyiminoacetateYield 58.3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

85 g of ethyl 4-bromo-2-propoxyimino-acetoacetate are added dropwise to 23 g (0.3 mole) of thiourea in 155 ccs of water and 75 ccs of ethanol at 25°, while stirring. After one hour, the hydrobromide which has precipitated in the meantime is decomposed by adding concentrated ammonia up to pH 6. After filtering off the product, washing with water and diisopropyl ether and drying, 45 g of ethyl 2-(2-aminothiazol-4-yl)-2-propoxyimino-acetate are obtained.

Workup

  1. customthe hydrobromide which has precipitated in the meantime
  2. additionby adding concentrated ammonia up to pH 6
  3. filtrationAfter filtering off the product
  4. washwashing with water and diisopropyl ether
  5. customdrying

Sources & evidence

ORD record
ord-a13c9bb6f00c45ebacf02a91d0c1c6f7
Source dataset
uspto-grants-1983_08
Patent number
US04399131

Reaction notes

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