4-Chlorobenzenesulfonyl chloride → Benzenesulfonamide, 4-chloro-N-(2-hydroxyethyl)-N-methyl-

HRID 1763756Notes

Reaction equation

HRID 1763756 reaction equation
[CH3:1][NH:2][CH2:3][CH2:4][OH:5].[Cl:6][C:7]1[CH:12]=[CH:11][C:10]([S:13](Cl)(=[O:15])=[O:14])=[CH:9][CH:8]=1>O1CCCC1>[CH3:1][N:2]([CH2:3][CH2:4][OH:5])[S:13]([C:10]1[CH:11]=[CH:12][C:7]([Cl:6])=[CH:8][CH:9]=1)(=[O:15])=[O:14]

Participants

4

Reactant 2

HCID 73984-Chlorobenzenesulfonyl chlorideHCID 80162-(Methylamino)ethanol

Product 1

HCID 108691Benzenesulfonamide, 4-chloro-N-(2-hydroxyethyl)-N-methyl-

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
50 °C

Procedure

To 20 parts of tetrahydrofuran is added 3.9 parts of N-methyl-ethanolamine. To this solution, 10 parts of tetrahydrofuran containing 5 parts of p-chlorobenzenesulfonyl chloride is added with stirring. After completion of the addition, the resultant mixture is stirred as it is for a while, and then heated for about 1 hour on a water bath at 50° C. to terminate the reaction. Then, the salt is removed by filtration, and the filtrate is freed from the solvent, whereby an oily substance is obtained. This oily substance is subjected to distillation under reduced pressure to obtain 4.2 parts of a distillate, b.p. 180° C./0.5 mmHg.

Workup

  1. additionAfter completion of the addition
  2. customto terminate
  3. customthe reaction
  4. customThen, the salt is removed by filtration
  5. customis obtained
  6. distillationThis oily substance is subjected to distillation under reduced pressure
  7. customto obtain 4.2 parts of a distillate, b.p. 180° C./0.5 mmHg

Sources & evidence

ORD record
ord-5f6c9c12dad547abb9366f118ec830bb
Source dataset
uspto-grants-1978_09
Patent number
US04113463

Reaction notes

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