Methyl p-toluenesulfonate → Benzothiazolium, 3-methyl-2-(methylthio)-, 4-methylbenzenesulfonate (1:1)

HRID 1699966Notes

Reaction equation

HRID 1699966 reaction equation
[N+]([C:4]1[CH:14]=[CH:13][C:7]2[N:8]=[C:9]([S:11][CH3:12])[S:10][C:6]=2[CH:5]=1)([O-])=O.[CH3:15][O:16][S:17]([C:20]1[CH:25]=[CH:24][C:23]([CH3:26])=[CH:22][CH:21]=1)(=[O:19])=[O:18]>CCOCC>[C:23]1([CH3:26])[CH:22]=[CH:21][C:20]([S:17]([O-:19])(=[O:16])=[O:18])=[CH:25][CH:24]=1.[CH3:15][N+:8]1[C:7]2[CH:13]=[CH:14][CH:4]=[CH:5][C:6]=2[S:10][C:9]=1[S:11][CH3:12]

Participants

4

Reactant 2

HCID 6645Methyl p-toluenesulfonateHCID 3055522-(Methylthio)-6-nitro-1,3-benzothiazole

Product 1

HCID 41464Benzothiazolium, 3-methyl-2-(methylthio)-, 4-methylbenzenesulfonate (1:1)Yield 63.6%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

A mixture of 0.5 g (2.2 mmol) of 6-nitro-2-(methylthio)benzothiazole (7) and 3.7 g (20 mmol) methyl-p-toluensulfonate was heated from 120° C. to 145° C. over one hour. The solution was allowed to cool, and to it was added 30 ml of ether. The resulting amorphous solid was triturated with acetone to provide 0.57 g (1.4 mmol, 63%) of 8 as a pale, mauve solid.

Workup

  1. temperaturewas heated from 120° C. to 145° C. over one hour
  2. temperatureto cool
  3. customThe resulting amorphous solid was triturated with acetone

Sources & evidence

ORD record
ord-fd0fc1fa7e3b4db78cbba82e8429253e
Source dataset
uspto-grants-2002_02
Patent number
US06348596B1

Reaction notes

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