Phosphorus oxychloride → 3,4-Dichloro-1,2-benzothiazole

반응식

P(Cl)(Cl)([Cl:3])=O.[Cl:6][C:7]1[C:12]2[C:13](=O)[NH:14][S:15][C:11]=2[CH:10]=[CH:9][CH:8]=1>>[Cl:3][C:13]1[C:12]2[C:7]([Cl:6])=[CH:8][CH:9]=[CH:10][C:11]=2[S:15][N:14]=1

참가 물질

반응물 2

HCID 24813Phosphorus oxychloride

HCID 574365604-Chloro-2,3-dihydro-1,2-benzothiazol-3-one

생성물 1

HCID 198345773,4-Dichloro-1,2-benzothiazole

실험 절차

Phosphorus oxychloride was added slowly to 4-chlorobenzo[d]isothiazol-3(2H)-one (2.34 g). The reaction mixture was heated at reflux overnight. After normal aqueous work-up, the product was purified by column chromatography, on silica gel, eluted with a mixture of 5% ethyl acetate in hexanes to provide 3,4-dichlorobenzo[d]isothiazole. (This method can be used to 1,2-benzisothiozal-3-ones). 1H NMR (300 MHz, DMSO-d6): 8.23-8.31 (m, 1H), 7.62 ppm (d, 2H). MW=204 confirmed by LC-MS, tr=2.38 min (Method B) MH+=205.

후처리

temperatureThe reaction mixture was heated
temperatureat reflux overnight
customAfter normal aqueous work-up, the product was purified by column chromatography, on silica gel
washeluted with a mixture of 5% ethyl acetate in hexanes

출처 및 근거

ORD 기록: ord-c15249ddf2d3475da2688eb18e0542e9
출처 데이터셋: uspto-grants-2010_08
DOI: 10.6084/m9.figshare.5104873.v1
특허 번호: US07776847B2

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