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

HRID 409703Notes

Reaction equation

[CH2:1]([N:7]([CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH3:26])[S:8]([C:11]1[CH:20]=[CH:19][C:14]2[N:15]=[C:16]([CH3:18])[S:17][C:13]=2[CH:12]=1)(=[O:10])=[O:9])[CH2:2][CH2:3][CH2:4][CH2:5][CH3:6].[CH3:27][O:28][S:29]([C:32]1[CH:37]=[CH:36][C:35]([CH3:38])=[CH:34][CH:33]=1)(=[O:31])=[O:30].CCCCCC>C(OCC)(=O)C>[S:29]([C:32]1[CH:37]=[CH:36][C:35]([CH3:38])=[CH:34][CH:33]=1)([O-:31])(=[O:30])=[O:28].[CH2:21]([N:7]([CH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH3:6])[S:8]([C:11]1[CH:20]=[CH:19][C:14]2[N+:15]([CH3:27])=[C:16]([CH3:18])[S:17][C:13]=2[CH:12]=1)(=[O:10])=[O:9])[CH2:22][CH2:23][CH2:24][CH2:25][CH3:26]

Participants

Conditions

Temperature: 130 °C

Procedure

A mixture of Compound 20 (2.0 g, 5.0 mmol) and p-toluenesulfonic acid methyl ester (1.4 g, 7.5 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 dissolved in ethyl acetate (4 ml). The combined mixture was then added drop wise to hexane (40 ml). A sticky dark brown solid separated which was washed with hexane and dried under vacuum to yield 2.3 g (78%) of Compound 21 which was used without any further purification. The structure of this compound is given below:

Workup

temperatureto cool to room temperature
customA sticky dark brown solid separated which
washwas washed with hexane
customdried under vacuum

Sources & evidence

ORD record: ord-cb8cbd08282c4cc2b4c8a89c9e73fceb
Source dataset: uspto-grants-2014_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08759526B2

Reaction notes

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