Benzoyl isothiocyanate → 1-Benzoyl-3-(2,5-dibromo-phenyl)-thiourea

HRID 2068671Notes

Reaction equation

HRID 2068671 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([Br:8])=[CH:4][C:3]=1[NH2:9].[C:10]([N:18]=[C:19]=[S:20])(=[O:17])[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1>CC(C)=O>[C:10]([NH:18][C:19]([NH:9][C:3]1[CH:4]=[C:5]([Br:8])[CH:6]=[CH:7][C:2]=1[Br:1])=[S:20])(=[O:17])[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1

Participants

4

Reactant 2

HCID 68284Benzoyl isothiocyanateHCID 771982,5-Dibromoaniline

Product 1

HCID 596030861-Benzoyl-3-(2,5-dibromo-phenyl)-thioureaYield 97%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To a solution of 2,5-dibromo-phenylamine I (2.44 g, 9.72 mmol) in acetone (60 mL) was added benzoylisothiocyanate (1.74 g, 26.0 mL, 10.6 mmol) at room temperature. After 15 min, solid precipitated out. The reaction mixture was continued to stir for 30 min at room temperature. After completion of reaction (TLC monitoring) acetone was distilled off and crude solid filtered with hexane (100 mL) and again washed with hexane (100 mL) to obtain the desired compound as pale-yellow solid (3.9 g, 97%). 1H NMR (DMSO-d6, 400 MHz): δ 7.47 (dd, J=6.4, 6.0 Hz, 1H), 7.53 (m, 2H), 7.66 (s, 1H), 7.70 (m, 1H), 7.99 (m, 1H), 8.01 (s, 1H), 8.17 (d, J=2.4 Hz, 1H), 11.91 (br s, 1H) and 12.63 (br s, 1H).

Workup

  1. customsolid precipitated out
  2. customAfter completion of reaction (TLC monitoring) acetone
  3. distillationwas distilled off
  4. filtrationcrude solid filtered with hexane (100 mL)
  5. washagain washed with hexane (100 mL)

Sources & evidence

ORD record
ord-8bd3d0b7e7204560a0bcc9104e44deab
Source dataset
uspto-grants-2012_10
Patent number
US08299065B2

Reaction notes

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