Ethanol → HCID 178512646, compound

HRID 2120068Notes

Reaction equation

HRID 2120068 reaction equation
[C:1]([NH2:7])([NH2:6])=[N:2][C:3]([NH2:5])=[S:4].Br[CH2:9][C:10](=O)[C:11]([O:13]CC)=[O:12].[NH4+].[OH-].[CH3:19][CH2:20]O>>[NH:2]([C:3]1[S:4][CH:19]=[C:20]([CH2:9][CH2:10][C:11]([OH:13])=[O:12])[N:5]=1)[C:1]([NH2:7])=[NH:6]

Participants

5

Reactant 4

HCID 702EthanolHCID 14923Ammonium HydroxideHCID 66144Ethyl bromopyruvate2×HCID 2724563Amidinothiourea

Product 1

HCID 178512646HCID 178512646, compound

Conditions

Temperature
10 °C

Procedure

To 2-imino-4-thiobiuret (11.1 g, 0.094 mole) (Aldrich) in absolute EtOH (100 mL) and at reflux was added ethyl bromopyruvate (20.0 g, 0.102 mole) (Aldrich) portionwise. The solution was stirred at reflux for 2 hours. Additional ethyl bromopyruvate (2.0 g) was added and the reaction continued at reflux for 2 more hours. The reaction was cooled to 10° C. and concentrated NH4OH was added until pH=10. The resulting precipitate was filtered, washed with ether and dried to yield 2-guanidino-4-carboxyethylthiazole as a yellow solid (15.1 g).

Workup

  1. temperatureat reflux for 2 hours
  2. temperatureat reflux for 2 more hours
  3. filtrationThe resulting precipitate was filtered
  4. washwashed with ether
  5. customdried

Sources & evidence

ORD record
ord-3abf8efd3273447eba993e40a38f7f2e
Source dataset
uspto-grants-2004_02
Patent number
US06689754B1

Reaction notes

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