Ammonia → N-(Aminocarbonyl)-2-chlorobenzenesulfonamide

HRID 236520Notes

Reaction equation

HRID 236520 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[S:8]([N:11]=[C:12]=[O:13])(=[O:10])=[O:9].[NH3:14]>C1(C)C=CC=CC=1>[NH2:14][C:12]([NH:11][S:8]([C:3]1[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=1[Cl:1])(=[O:10])=[O:9])=[O:13]

Participants

4

Reactant 2

HCID 222AmmoniaHCID 174071Benzenesulfonyl isocyanate, 2-chloro-

Product 1

HCID 151248N-(Aminocarbonyl)-2-chlorobenzenesulfonamide

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
0 °C

Procedure

A solution of 314 g of 2-chlorobenzenesulfonyl isocyanate in 2 L of toluene was cooled to 0° C. and treated with 27 g of anhydrous liquid ammonia, added dropwise at a rate that maintained the temperature around 0° C. After the addition was complete, the reaction mixture was allowed to warm to room temperature. The solids were collected by filtration, and washed with hexane and acetonitrile. The yield of N-(aminocarbonyl)-2-chlorobenzenesulfonamide was 313 g as a white solid, m.p. 160°-163° C.; IR (nujol): 3400, 3300, 1700, 1650, 1550, 1250, 1150 cm-1.

Workup

  1. additionadded dropwise at a rate that
  2. additionAfter the addition
  3. temperatureto warm to room temperature
  4. filtrationThe solids were collected by filtration
  5. washwashed with hexane and acetonitrile

Sources & evidence

ORD record
ord-f4062c7f99fe4a88b2d818991c90690c
Source dataset
uspto-grants-1987_02
Patent number
US04645527

Reaction notes

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