Bromine → HCID 18953809, compound

HRID 2379845Notes

Reaction equation

HRID 2379845 reaction equation
[Br:1]Br.[C:3]([C:6]1[N:7]=[C:8]([C:11]([NH2:13])=[O:12])[S:9][CH:10]=1)(=[O:5])[CH3:4]>CO>[Br:1][CH2:4][C:3]([C:6]1[N:7]=[C:8]([C:11]([NH2:13])=[O:12])[S:9][CH:10]=1)=[O:5]

Participants

4

Reactant 2

HCID 24408BromineHCID 18953789HCID 18953789, compound

Product 1

HCID 18953809HCID 18953809, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Bromine (1.3 g) was added slowly to a suspension of 4-acetylthiazole-2-carboxamide (1.3 g) in methanol (50 ml). The mixture was stirred for 3.5 hours at room temperature. The solvent was removed under reduced pressure to give 4-bromoacetylthiazole-2-carboxamide. The above residue and diaminomethylenethiourea (900 mg) were suspended in ethanol (50 ml) and the mixture was refluxed for 24 hours. The resulting precipitate was collected by filtration and suspended in water (50 ml). The mixture was alkalized to pH 11 with a saturated aqueous potassium carbonate solution. The resulting precipitate was collected by filtration. Recrystallization from methanol afforded 4-[2-(diaminomethyleneamino)thiazol-4-yl]thiazole-2-carboxamide (1.05 g).

Workup

  1. customThe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-e74b8450dcfe4ea58eda8e2541f5c560
Source dataset
uspto-grants-1994_11
Patent number
US05364871

Reaction notes

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