Benzenesulfonyl chloride → HCID 3856345, compound

HRID 224531Notes

Reaction equation

HRID 224531 reaction equation
C[N:2]([C:12]([CH3:20])([CH3:19])[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)[S:3]([C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)(=[O:5])=[O:4].CC(N)(C)C1C=CC=CC=1.[OH-].[Na+].C1(S(Cl)(=O)=O)C=CC=CC=1>>[CH3:20][C:12]([NH:2][S:3]([C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)(=[O:4])=[O:5])([CH3:19])[C:13]1[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=1

Participants

5

Reactant 4

HCID 7369Benzenesulfonyl chlorideHCID 14798Sodium HydroxideHCID 68509CumylamineHCID 22164290HCID 22164290, compound

Product 1

HCID 3856345HCID 3856345, compoundYield 67%

Procedure

The N-(α,α-dimethylbenzyl)benzenesulfonamide used as a starting compound in the above procedure could be prepared in the following manner. A two-layered mixture consisting of 33.8 g (0.25 mole) of α,α-dimethylbenzylamine and 120 ml of a 10% aqueous solution of sodium hydroxide was stirred at below 40° C., and 44.1 g of benzenesulfonyl chloride was added dropwise. Stirring the mixture for an additional 1.5 hours afforded a white precipitate. The solid precipitate was collected by filtration, and recrystallized from methanol to afford N-(α,α-dimethylbenzyl)benzenesulfonamide having melting point of 114° to 115° C. in a yield of 67%.

Workup

  1. customcould be prepared in the following manner
  2. stirringStirring the mixture for an additional 1.5 hours
  3. customafforded a white precipitate
  4. filtrationThe solid precipitate was collected by filtration
  5. customrecrystallized from methanol

Sources & evidence

ORD record
ord-2ecfb2d865554aabbca384edde436de7
Source dataset
uspto-grants-1980_11
Patent number
US04233061

Reaction notes

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