Water → P-Toluenesulfonamide

HRID 2164037Notes

Reaction equation

HRID 2164037 reaction equation
ClC1C(Cl)=CC=CC=1[NH2:4].N1C=CC=CC=1.O.[C:17]1([CH3:27])[CH:22]=[CH:21][C:20]([S:23](Cl)(=[O:25])=[O:24])=[CH:19][CH:18]=1>>[CH3:27][C:17]1[CH:22]=[CH:21][C:20]([S:23]([NH2:4])(=[O:25])=[O:24])=[CH:19][CH:18]=1

Participants

5

Reactant 4

HCID 962WaterHCID 1049PyridineHCID 73974-Toluenesulfonyl chlorideHCID 118442,3-Dichloroaniline

Product 1

HCID 6269P-ToluenesulfonamideYield 175.8%

Conditions

Temperature
50 °C

Procedure

A solution of 2,3-dichloroaniline (162.0 g) in p-toluenesulfonyl chloride (190.7 g) is heated at 100° C. for one hour allowing the temperature to rise to 115° C. with the exotherm. The thick mixture is then cooled to 50° C. and pyridine (250 ml) is added carefully. The reaction mixture exotherms to 150° C. After stirring for one hour the mixture is cooled and poured into water (2.5 liter). The precipitated solid is collected and dried to yield 301 g of tosylamide, m.p. 112°-118° C.

Workup

  1. customto rise to 115° C. with the exotherm
  2. customexotherms to 150° C
  3. temperatureis cooled
  4. customThe precipitated solid is collected
  5. customdried

Sources & evidence

ORD record
ord-ca2b2d3228234e7aa18cae83c699dc4e
Source dataset
uspto-grants-1979_01
Patent number
US04137310

Reaction notes

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