p-Toluenesulfonic acid monohydrate → HCID 178483688, compound

HRID 2116851Notes

Reaction equation

HRID 2116851 reaction equation
[CH3:1][N:2]([C:4]([N:7]([CH3:9])[CH3:8])(Cl)[Cl:5])[CH3:3].O.[C:11]1([CH3:21])[CH:16]=[CH:15][C:14]([S:17]([OH:20])(=[O:19])=[O:18])=[CH:13][CH:12]=1>>[S:17]([C:14]1[CH:15]=[CH:16][C:11]([CH3:21])=[CH:12][CH:13]=1)([O-:20])(=[O:19])=[O:18].[CH3:1][N:2]([C+:4]([N:7]([CH3:9])[CH3:8])[Cl:5])[CH3:3]

Participants

3

Reactant 2

HCID 521998p-Toluenesulfonic acid monohydrateHCID 125447451,1-Dichloro-N,N,N',N'-tetramethylmethanediamine

Product 1

HCID 178483688HCID 178483688, compoundYield 97.8%

Conditions

Temperature
100 °C

Procedure

3.0 g (17.5 mmol) of bis(dimethylamino)dichloromethane and 3.33 g (17.5 mmol) of p-toluenesulfonic acid monohydrate are mixed. The mixture is heated to 100° C. over the course of 30 min, and a vacuum of 7 Pa is subsequently applied over one hour. Cooling to room temperature gives 5.25 g of bis(dimethylamino)chlorocarbenium tosylate, corresponding to a yield of 97.8%.

Workup

  1. temperatureCooling to room temperature

Sources & evidence

ORD record
ord-5d6d8340f5d0416387a6d94e3c2fbfd6
Source dataset
uspto-grants-2008_10
Patent number
US07439395B2

Reaction notes

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