Benzoyl isothiocyanate → SBB062200

HRID 2110043Notes

Reaction equation

HRID 2110043 reaction equation
[C:1]([N:9]=[C:10]=[S:11])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:12][O:13][C:14]([C:16]1[S:17][CH:18]=[CH:19][C:20]=1[NH2:21])=[O:15]>CC(C)=O>[CH3:12][O:13][C:14]([C:16]1[S:17][CH:18]=[CH:19][C:20]=1[NH:21][C:10]([NH:9][C:1]([C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)=[O:8])=[S:11])=[O:15]

Participants

4

Reactant 2

HCID 68284Benzoyl isothiocyanateHCID 89652Methyl 3-amino-2-thiophenecarboxylate

Product 1

HCID 1481005SBB062200

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent2×

Procedure

A solution of benzoyl isothiocyanate (1038 mg, 6.36 mmol) in acetone (3 mL) was added to absolution of 3-aminothiophene-2-carboxylic acid methyl ester (500 mg, 3.18 mmol) in acetone (3 mL). The mixture was stirred at room temperature for 10 hours and then concentrated, and the residue was purified by silica gel chromatography (Hex/EtOAc=10/1) to obtain 3-{[(phenylcarbonylamino) thioxomethyl]amino}thiophene-2-carboxylic acid methyl ester.

Workup

  1. concentrationconcentrated
  2. customthe residue was purified by silica gel chromatography (Hex/EtOAc=10/1)

Sources & evidence

ORD record
ord-74dcce8dba2340f78389e263f0b16647
Source dataset
uspto-grants-2009_04
Patent number
US07517875B2

Reaction notes

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