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

HRID 1941975Notes

Reaction equation

HRID 1941975 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-286190a5068c43a6ad25e27f005dd73e
Source dataset
uspto-grants-2013_03
Patent number
US08389516B2

Reaction notes

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