Carbon Disulfide → 4-Bromo-1-isothiocyanato-2-methylbenzene

HRID 1736400Notes

Reaction equation

HRID 1736400 reaction equation
[Br:1][C:2]1[CH:8]=[CH:7][C:5]([NH2:6])=[C:4]([CH3:9])[CH:3]=1.C1(N=C=NC2CCCCC2)CCCCC1.[C:25](=S)=[S:26]>N1C=CC=CC=1.C(N(CC)CC)C>[Br:1][C:2]1[CH:8]=[CH:7][C:5]([N:6]=[C:25]=[S:26])=[C:4]([CH3:9])[CH:3]=1

Participants

6

Reactant 3

HCID 6348Carbon DisulfideHCID 10868DicyclohexylcarbodiimideHCID 114234-Bromo-2-methylaniline

Product 1

HCID 879774-Bromo-1-isothiocyanato-2-methylbenzene

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 8471TriethylamineSolvent

Procedure

In 800 ml of pyridine were dissolved 275 ml of carbon disulfide and 93 ml of triethylamine. To the solution was added 125 g of 4-bromo-2-methylaniline. The mixture was stirred at room temperature overnight. Thereto was added 138.5 g of 1,3-dicyclohexylcarbodiimide (DCC). The mixture was stirred overnight. Pyridine was removed by distillation. To the residue was added n-hexane. The resulting precipitate (DC-thiourea) was removed by filtration. The filtrate was concentrated and the residue was purified by a silica gel column chromatography (eluant: n-hexane) to obtain 138 g of 4-bromo-2-methylphenyl isothiocyanate.

Workup

  1. stirringThe mixture was stirred overnight
  2. customPyridine was removed by distillation
  3. additionTo the residue was added n-hexane
  4. customThe resulting precipitate (DC-thiourea) was removed by filtration
  5. concentrationThe filtrate was concentrated
  6. customthe residue was purified by a silica gel column chromatography (eluant: n-hexane)

Sources & evidence

ORD record
ord-eb01b3a8293b49999db6481d2e1e379b
Source dataset
uspto-grants-1996_07
Patent number
US05541198

Reaction notes

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