4-Chloroaniline → LY 181984

HRID 651493

Reaction equation

HRID 651493 reaction equation
[Cl:1][C:2]1[CH:8]=[CH:7][C:5]([NH2:6])=[CH:4][CH:3]=1.[C:9]1([CH3:21])[CH:14]=[CH:13][C:12]([S:15]([N:18]=[C:19]=[O:20])(=[O:17])=[O:16])=[CH:11][CH:10]=1>C(Cl)Cl>[Cl:1][C:2]1[CH:8]=[CH:7][C:5]([NH:6][C:19]([NH:18][S:15]([C:12]2[CH:13]=[CH:14][C:9]([CH3:21])=[CH:10][CH:11]=2)(=[O:17])=[O:16])=[O:20])=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 78124-ChloroanilineHCID 77703p-Toluenesulfonyl isocyanate

Product 1

HCID 160725LY 181984Yield 94.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Procedure

A solution of 6.25 g (49.00 mmoles) of 4-chloroaniline in 10 ml of methylene chloride was added to a solution of 9.85 g (49.95 mmoles) of p-toluenesulfonyl isocyanate in 75 ml of methylene chloride with stirring. The mixture became quite warm and a heavy white precipitate formed. An additional 100 ml of methylene chloride were added. The reaction mixture was stirred an additional 15 minutes, and the precipitate was recovered by filtration affording 15.0 g of the title product as a white solid. A small amount of the material was crystallized from diethyl ether to provide the title compound (87% yield) with a melting point of 174-176_C.

Workup

  1. temperatureThe mixture became quite warm
  2. customa heavy white precipitate formed
  3. stirringThe reaction mixture was stirred an additional 15 minutes
  4. filtrationthe precipitate was recovered by filtration

Sources & evidence

ORD record
ord-1760152cf4e848c6a7a57f68ac077b82
Source dataset
uspto-grants-2001_08
Patent number
US06281240B1

Linked notes

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