Benzoyl isothiocyanate → 1-Benzoyl-3-(5-bromo-2,4-difluoro-phenyl)-thiourea

HRID 1399975Notes

Reaction equation

HRID 1399975 reaction equation
[Br:1][C:2]1[C:3]([F:10])=[CH:4][C:5]([F:9])=[C:6]([CH:8]=1)[NH2:7].[C:11]([N:19]=[C:20]=[S:21])(=[O:18])[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1>CC(C)=O>[C:11]([NH:19][C:20]([NH:7][C:6]1[CH:8]=[C:2]([Br:1])[C:3]([F:10])=[CH:4][C:5]=1[F:9])=[S:21])(=[O:18])[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Participants

4

Reactant 2

HCID 68284Benzoyl isothiocyanateHCID 27832955-Bromo-2,4-difluoroaniline

Product 1

HCID 596030931-Benzoyl-3-(5-bromo-2,4-difluoro-phenyl)-thiourea

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To a solution of 5-bromo-2,4-difluoro-aniline (1.0 g, 4.81 mmol) in acetone (25.0 mL) was added drop wise benzoyl isothiocyanate (0.71 mL, 5.29 mmol) and the mixture stirred at RT for 30 min. The solvent was evaporated and the residue washed with hexane and Et2O to get i (1.70 g). 1H-NMR (400 MHz, CDCl3): δ 7.02-7.06 (m, 1H), 7.56 (t, J=8.0 Hz, 2H), 7.68 (t, J=7.60 Hz, 1H), 7.91 (d, J=7.60 Hz, 2H), 8.67 (t, J=7.60 Hz, 1H), 9.15 (br s, 1H) and 12.65 (br s, 1H).

Workup

  1. customThe solvent was evaporated
  2. washthe residue washed with hexane and Et2O
  3. customto get i (1.70 g)

Sources & evidence

ORD record
ord-02dc9483b4594121ae871165899c3332
Source dataset
uspto-grants-2014_12
Patent number
US08906902B2

Reaction notes

Loading…