Benzoyl isothiocyanate → SBB062200

HRID 539857Notes

Reaction equation

HRID 539857 reaction equation
[CH3:1][O:2][C:3]([C:5]1[S:6][CH:7]=[CH:8][C:9]=1[NH2:10])=[O:4].[C:11]([N:19]=[C:20]=[S:21])(=[O:18])[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1>CC(C)=O>[C:12]1([C:11]([NH:19][C:20](=[S:21])[NH:10][C:9]2[CH:8]=[CH:7][S:6][C:5]=2[C:3]([O:2][CH3:1])=[O:4])=[O:18])[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Participants

4

Reactant 2

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

Product 1

HCID 1481005SBB062200

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

Methyl-3-amino-2-thiophene carboxylate (30 g, 1 equiv) and benzoyl isothiocyanate (46 ml, 1.8 equiv) in acetone (250 ml) were heated to 65° C. for 30 minutes. After cooling the solution was concentrated and the resulting solid filtered off and dried (40.54 g). 1H-NMR (CDCl3) δ 3.98 (3H, s), 7.54 (4H, m), 7.94 (2H, m), 8.81 (1H, d), 9.15 (1H, br s); MS (APCI+) found (M+1)=321; C14H12N2O3S2 requires 320.

Workup

  1. temperatureAfter cooling the solution
  2. concentrationwas concentrated
  3. filtrationthe resulting solid filtered off
  4. customdried (40.54 g)

Sources & evidence

ORD record
ord-91d69c954c9a4ab6804f1913f1d6a299
Source dataset
uspto-grants-2014_10
Patent number
US08871775B2

Reaction notes

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