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

HRID 1399961Notes

Reaction equation

HRID 1399961 reaction equation
[CH2:1]([O:8][C:9]1[CH:10]=[C:11]([CH:13]=[C:14]([Br:16])[CH:15]=1)[NH2:12])[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>[CH2:1]([O:8][C:9]1[CH:10]=[C:11]([NH:12][C:26]([NH:25][C:17](=[O:24])[C:18]2[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=2)=[S:27])[CH:13]=[C:14]([Br:16])[CH:15]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

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

Product 1

HCID 57813640N-[(3-benzyloxy-5-bromophenyl)carbamothioyl]benzamide

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Conditions

Temperature
40 °C

Procedure

To a solution of iv (480 g, 1.73 mol) in acetone (10 L) was added benzoylisothiocyanate (280 mL, 2.08 mol) at RT and the mixture stirred for 45 min. The acetone was distilled off and hexane (2 L) added and the mixture concentrated to dryness. To the residue was added hexane (4 L) and the mixture heated to 40° C. for 30 min The solid was collected by filtration and washed with hexane (2×2 L) to obtain v (648 g, 85%).

Workup

  1. distillationThe acetone was distilled off
  2. additionhexane (2 L) added
  3. concentrationthe mixture concentrated to dryness
  4. additionTo the residue was added hexane (4 L)
  5. filtrationwas collected by filtration
  6. washwashed with hexane (2×2 L)
  7. customto obtain v (648 g, 85%)

Sources & evidence

ORD record
ord-e58cf50c78eb4487bdd6d35c93de77b6
Source dataset
uspto-grants-2014_12
Patent number
US08906902B2

Reaction notes

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