Thiourea → HCID 59375349, compound

HRID 1667658Notes

Reaction equation

HRID 1667658 reaction equation
Br[CH:2]([C:6]([C:8]1[CH:13]=[CH:12][C:11]([Cl:14])=[CH:10][CH:9]=1)=O)[C:3]([NH2:5])=[O:4].[NH2:15][C:16]([NH2:18])=[S:17]>C(O)C>[NH2:18][C:16]1[S:17][C:2]([C:3]([NH2:5])=[O:4])=[C:6]([C:8]2[CH:13]=[CH:12][C:11]([Cl:14])=[CH:10][CH:9]=2)[N:15]=1

Participants

4

Reactant 2

HCID 2723790ThioureaHCID 86642795HCID 86642795, compound

Product 1

HCID 59375349HCID 59375349, compoundYield 16.5%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a mixture of 7.35 g (26.58 mmole) of 2-bromo-3-(4-chloro-phenyl)-3-oxo-propionamide and 300 mL of ethanol was added 2.02 g (26.58 mmole) of thiourea. The mixture was stirred at room temperature for 4 hours and then concentrated under reduced pressure. The residue was purified by silica gel chromatography, eluting with ethyl acetate-dichloromethane (1:3, then 3:1, then 1:0). Recrystallization of the residue gave 1.11 g of 2-amino-4-(4-chloro-phenyl)-thiazole-5-carboxylic acid amide (V.18) as pale yellow crystals.

Workup

  1. concentrationconcentrated under reduced pressure
  2. customThe residue was purified by silica gel chromatography
  3. washeluting with ethyl acetate-dichloromethane (1:3
  4. customRecrystallization of the residue

Sources & evidence

ORD record
ord-5a1cb5cc37a44c05a29a5457daad44bd
Source dataset
uspto-grants-2011_10
Patent number
US08044213B2

Reaction notes

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