Ethyl bromopyruvate → HCID 178419569, compound

HRID 611596

Reaction equation

HRID 611596 reaction equation
[Br:1][CH2:2][C:3](=O)[C:4]([O:6][CH2:7][CH3:8])=[O:5].[C:10]([NH2:16])([NH2:15])=[N:11][C:12]([NH2:14])=[S:13]>C(O)C>[BrH:1].[NH:11]([C:12]1[S:13][CH:2]=[C:3]([C:4]([O:6][CH2:7][CH3:8])=[O:5])[N:14]=1)[C:10]([NH2:16])=[NH:15]

Participants

4

Reactant 2

HCID 66144Ethyl bromopyruvateHCID 2724563Amidinothiourea

Product 1

HCID 178419569HCID 178419569, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

13.9 ml of ethyl bromopyruvate are added to a solution of 11.81 g of 2-imino-4-thiobiuret (Aldrich) in 100 ml of ethanol and the reaction mixture is heated under reflux for 3 hours (J. Med. Chem. 34, 914-918 (1991)). Subsequently, the mixture is cooled to room temperature and the reaction product is precipitated by the addition of 550 ml of ethyl acetate and filtered off. There are obtained 14.6 g of yellowish ethyl 2-guanidino-thiazole-4-carboxylate hydrobromide. MS: 214 (M)+.

Workup

  1. temperaturethe reaction mixture is heated
  2. temperatureunder reflux for 3 hours (J. Med. Chem. 34, 914-918 (1991))
  3. customthe reaction product is precipitated by the addition of 550 ml of ethyl acetate
  4. filtrationfiltered off

Sources & evidence

ORD record
ord-f50c18ad823042108b859b83988eafec
Source dataset
uspto-grants-1999_12
Patent number
US06001855

Linked notes

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