Benzenesulfonyl chloride → N-(2-pyridyl)-4-(benzenesulfonyl)-2-methyl-2H-1,2-benzothiazine-3-carboxamide 1,1-dioxide

HRID 2119206Notes

Reaction equation

[CH3:1][N:2]1[CH:7]([C:8]([OH:10])=O)[C:6](=O)[C:5]2[CH:12]=[CH:13][CH:14]=[CH:15][C:4]=2[S:3]1(=[O:17])=[O:16].C(N(CC)CC)C.[C:25]1([S:31](Cl)(=[O:33])=[O:32])[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1.[NH2:35][C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][N:37]=1>O1CCCC1>[N:37]1[CH:38]=[CH:39][CH:40]=[CH:41][C:36]=1[NH:35][C:8]([C:7]1[N:2]([CH3:1])[S:3](=[O:17])(=[O:16])[C:4]2[CH:15]=[CH:14][CH:13]=[CH:12][C:5]=2[C:6]=1[S:31]([C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)(=[O:33])=[O:32])=[O:10]

Participants

Conditions

Temperature: -5 °C

Procedure

1.29 g (0.005 mole) 3,4-dihydro-2-methyl-4-oxo-2H-1,2-benzothiazine-3-carboxylic acid 1,1-dioxide and 4.18 ml triethylamine were dissolved in 15 ml tetrahydrofuran and the mixture cooled to -5° C. and 1.91 ml benzenesulfonyl chloride was added slowly to the stirred mixture and stirred, and after one hour 0.52 g 2-aminopyridine was added to the mixture. The temperature of the mixture was raised slowly to ambient temperature and stirred for 4 hours, and twice the volume of ice water was added to the mixture to form precipitates. The obtained precipitates were filtered and recrystallized in ethanol and ethylether to obtain 1.6 g of the title compound. Yield: 68%. m.p 192°-195° C.

Workup

temperatureThe temperature of the mixture was raised slowly to ambient temperature
stirringstirred for 4 hours
customto form
customprecipitates
customThe obtained precipitates
filtrationwere filtered
customrecrystallized in ethanol

Sources & evidence

ORD record: ord-4fd2ec96af0046709b7d376dc9f8532c
Source dataset: uspto-grants-1987_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04683306

Reaction notes

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