Benzoyl isothiocyanate → N-[(3-benzyloxy-5-bromophenyl)carbamothioyl]benzamide

HRID 1010684Notes

Reaction equation

HRID 1010684 reaction equation
[CH2:1]([O:8][C:9]1[CH:10]=[C:11]([NH2:16])[CH:12]=[C:13]([Br:15])[CH:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:17]([N:25]=[C:26]=[S:27])(=[O:24])[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1>CC(C)=O>[C:17]([NH:25][C:26]([NH:16][C:11]1[CH:12]=[C:13]([Br:15])[CH:14]=[C:9]([O:8][CH2:1][C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)[CH:10]=1)=[S:27])(=[O:24])[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1

Participants

4

Reactant 2

HCID 68284Benzoyl isothiocyanateHCID 578136263-(Benzyloxy)-5-bromoaniline

Product 1

HCID 57813640N-[(3-benzyloxy-5-bromophenyl)carbamothioyl]benzamideYield 89%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To a solution of 3-benzyloxy-5-bromo-phenylamine (23.50 g, 84.40 mmol) in acetone (550.0 mL) was added benzoyl isothiocyanate (18.50 mL, 93.13 mmol) and the reaction mixture was stirred at room temperature for 30 min. After the completion of the reaction (TLC monitoring), the solvent was evaporated and the residue thus obtained was washed with hexane to get the desired product (33.0 g, 89%).

Workup

  1. customAfter the completion of the reaction (TLC monitoring)
  2. customthe solvent was evaporated
  3. customthe residue thus obtained
  4. washwas washed with hexane

Sources & evidence

ORD record
ord-36c4fb42e2de4ff893242813afa30586
Source dataset
uspto-grants-2011_07
Patent number
US07977340B2

Reaction notes

Loading…