Dimethylformamide → (Aminothiocarbonyl)amino-5-phenyl-3-thiophenecarboxamide

HRID 900453Notes

Reaction equation

HRID 900453 reaction equation
[NH2:1][C:2]1[S:3][C:4]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)=[CH:5][C:6]=1[C:7]([NH2:9])=[O:8].C[Si]([N:20]=[C:21]=[S:22])(C)C.CN(C)C=O>CN(C)C(=O)C>[NH2:20][C:21]([NH:1][C:2]1[S:3][C:4]([C:10]2[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=2)=[CH:5][C:6]=1[C:7]([NH2:9])=[O:8])=[S:22]

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 75297IsothiocyanatotrimethylsilaneHCID 7039652-Amino-5-phenylthiophene-3-carboxamide

Product 1

HCID 9814203(Aminothiocarbonyl)amino-5-phenyl-3-thiophenecarboxamideYield 35.3%

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Procedure

A solution of 2-amino-5-phenyl-3-thiophenecarboxamide (1.09 g, 5 mmol) and trimethylsilyl isothiocyanate (0.85 ml, 6 mmol) in N,N-dimethylacetamide was stirred at 75° C. for 7 days. N,N-Dimethylformamide was added until solution. The solvent was removed and the resulting slurry was chromatographed on silica gel eluting with isohexane followed by methylene chloride and diethyl ether to give the product as a yellow solid (0.49 g, 35%).

Workup

  1. customThe solvent was removed
  2. customthe resulting slurry was chromatographed on silica gel eluting with isohexane

Sources & evidence

ORD record
ord-a9be78a2ef44464f81c5118eb59fb29c
Source dataset
uspto-grants-2008_04
Patent number
US07358376B2

Reaction notes

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