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

HRID 447054Notes

Reaction equation

HRID 447054 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-e68270707dc24592af027e14f13ffadb
Source dataset
uspto-grants-2013_07
Patent number
US08481544B2

Reaction notes

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