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

HRID 1834347Notes

Reaction equation

HRID 1834347 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-06267d990e584ad2911a17af6d3186b2
Source dataset
uspto-grants-1978_01
Patent number
US04070176

Reaction notes

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