Water → HCID 86665397, compound

HRID 2403039Notes

Reaction equation

HRID 2403039 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][C:10]=1[O:11][CH3:12])[C:5]([NH2:7])=[O:6].C([N:21]=[C:22]=[S:23])(=O)C1C=CC=CC=1.O>CC(C)=O>[CH3:12][O:11][C:10]1[CH:9]=[CH:8][C:4]([C:5]([NH2:7])=[O:6])=[CH:3][C:2]=1[NH:1][C:22]([NH2:21])=[S:23]

Participants

5

Reactant 3

HCID 962WaterHCID 68284Benzoyl isothiocyanateHCID 87135Benzamide, 3-amino-4-methoxy-

Product 1

HCID 86665397HCID 86665397, compound

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To a solution of 3-amino-4-methoxybenzamide (2.49 g, 15.0 mmol, Alfa) in acetone (30 mL) at reflux was added benzoyl isothiocyanate (2.22 mL, 16.5 mmol) and the mixture was stirred at reflux for 30 min, then was poured into water. The precipitate was collected by vacuum filtration and was treated with 10% aq. NaOH (15 mL). The mixture was heated to reflux for 40 min, cooled to room temperature, and poured into a mixture of ice and 6 N aq. HCl. The mixture was basified to pH 10 with conc. aq. NH4OH and the resulting white solid precipitate was collected by vacuum filtration, affording the crude title compound, which was used without further purification.

Workup

  1. temperatureat reflux for 30 min
  2. filtrationThe precipitate was collected by vacuum filtration
  3. additionwas treated with 10% aq. NaOH (15 mL)
  4. temperatureThe mixture was heated
  5. temperatureto reflux for 40 min
  6. additionpoured into a mixture of ice and 6 N aq. HCl
  7. filtrationthe resulting white solid precipitate was collected by vacuum filtration

Sources & evidence

ORD record
ord-0c862289ade24c6b860ecf39410e49bf
Source dataset
uspto-grants-2014_08
Patent number
US08798939B2

Reaction notes

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