Methyl p-toluenesulfonate → 6-(N,N-dimethylsulfamoyl)-2,3-dimethylbenzo[d]thiazole-3-ium tosylate

HRID 84782

Reaction equation

HRID 84782 reaction equation
[CH3:1][N:2]([CH3:16])[S:3]([C:6]1[CH:15]=[CH:14][C:9]2[N:10]=[C:11]([CH3:13])[S:12][C:8]=2[CH:7]=1)(=[O:5])=[O:4].[CH3:17][O:18][S:19]([C:22]1[CH:27]=[CH:26][C:25]([CH3:28])=[CH:24][CH:23]=1)(=[O:21])=[O:20]>>[S:19]([C:22]1[CH:27]=[CH:26][C:25]([CH3:28])=[CH:24][CH:23]=1)([O-:21])(=[O:20])=[O:18].[CH3:16][N:2]([CH3:1])[S:3]([C:6]1[CH:15]=[CH:14][C:9]2[N+:10]([CH3:17])=[C:11]([CH3:13])[S:12][C:8]=2[CH:7]=1)(=[O:4])=[O:5]

Participants

3

Reactant 2

HCID 6645Methyl p-toluenesulfonateHCID 14951224N,N,2-trimethylbenzo[d]thiazole-6-sulfonamide

Product 1

HCID 866093286-(N,N-dimethylsulfamoyl)-2,3-dimethylbenzo[d]thiazole-3-ium tosylateYield 84%

Conditions

Temperature
130 °C

Procedure

A mixture of Compound 24 (2.0 g, 7.8 mmol) and p-toluenesulfonic acid methyl ester (2.2 g, 11.7 mmol) was heated in a pressure tube at 130° C. for 2 hours. The mixture was allowed to cool to room temperature, and the resulting mass was triturated with ethyl acetate (25 ml) until an off-white solid separated. The solid was collected by centrifugation, washed with ethyl acetate and dried under vacuum to yield 2.9 g (84%) of Compound 25 whose structure is given

Workup

  1. temperatureto cool to room temperature
  2. customthe resulting mass was triturated with ethyl acetate (25 ml) until an off-white solid
  3. customseparated
  4. customThe solid was collected by centrifugation
  5. washwashed with ethyl acetate
  6. customdried under vacuum

Sources & evidence

ORD record
ord-82745570a0ff4f68b8b39938f2efcac6
Source dataset
uspto-grants-2014_09
Patent number
US08846952B2

Linked notes

Loading…