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

HRID 1942937Notes

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-466e19d98a5e43789e20497d3b142e53
Source dataset: uspto-grants-2013_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08389729B2

Reaction notes

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