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

HRID 712148Notes

Reaction equation

HRID 712148 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]benzamideYield 85%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Conditions

Temperature
40 °C

Procedure

To a solution of 3-benzyloxy-5-bromo-aniline (480 g, 1.73 mol) in acetone (10 L) was added benzoylisothiocyanate (280 mL, 2.08 mol) at rt. After stirring the reaction mixture for 15 min, solid precipitated out and stirring was continued for 30 min at rt. After completion of reaction (by TLC), acetone was distilled off. Hexane (2 L) was added and again concentrated. To the concentrated solid was added hexane (4 L) heated to 40° C. for 30 min under stirring and the solid filtered. The solid was washed with hexane (2×2 L) to obtain the desired product (648 g, 85%).

Workup

  1. customsolid precipitated out
  2. stirringstirring
  3. waitwas continued for 30 min at rt
  4. customAfter completion of reaction (by TLC), acetone
  5. distillationwas distilled off
  6. additionHexane (2 L) was added
  7. concentrationagain concentrated
  8. additionTo the concentrated solid was added hexane (4 L)
  9. stirringunder stirring
  10. filtrationthe solid filtered
  11. washThe solid was washed with hexane (2×2 L)

Sources & evidence

ORD record
ord-42d1b256812e4f4bb9a9e690709e631a
Source dataset
uspto-grants-2015_11
Patent number
US09181234B2

Reaction notes

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