P-Toluenesulfonamide → HCID 13674811, compound

HRID 1649978Notes

Reaction equation

HRID 1649978 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([CH3:8])[C:3]=1[NH:9][S:10]([CH3:13])(=[O:12])=[O:11].[CH3:14][C:15]1[CH:16]=CC(S(N)(=O)=O)=CC=1.[OH-:25].[Na+]>>[CH3:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([CH3:8])[C:3]=1[N:9]([CH2:14][CH:15]([OH:25])[CH3:16])[S:10]([CH3:13])(=[O:12])=[O:11]

Participants

4

Reactant 3

HCID 6269P-ToluenesulfonamideHCID 14798Sodium HydroxideHCID 686475HCID 686475, compound

Product 1

HCID 13674811HCID 13674811, compoundYield 75.5%

Procedure

20 g (0.1 moles) of N-(2,6-dimethylphenyl)-methane-sulfonamide, prepared as described by M. A. Bambenek [Rec. Trav. Chim. 82, 97 (1963)] for the corresponding p-toluenesulfonamide derivative, m.p.: 128°-129° C., are dissolved in 200 ml of 0.5 n aqueous sodium hydroxide solution under stirring. 12.7 ml (10.6 g, 0.18 moles) of 1,2-propylene-oxide are added dropwise to the solution at 80°-85° C. within 3 hours, and then the mixture is allowed to stand overnight. The separated crystalline substance is filtered off, washed with water and dried. 19.4 g (75.5%) of 1-[N-(2,6-dimethylphenyl)-methane-sulfonamido]-2-propanol are obtained; m.p.: 81°-84° C. When recrystallized from diisopropyl ether, the product melts at 85°-87° C.

Workup

  1. filtrationThe separated crystalline substance is filtered off
  2. washwashed with water
  3. customdried

Sources & evidence

ORD record
ord-082bf7d0c95149d6a1158a5f48a030dd
Source dataset
uspto-grants-1990_05
Patent number
US04922021

Reaction notes

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