Saccharin → 3,3-diphenyl-2H-1,2-benzothiazole 1,1-dioxide

HRID 1106138

반응식

HRID 1106138 반응식
[S:1]1([C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[C:5](=O)[NH:4]1)(=[O:3])=[O:2].[C:13]1([Mg]Br)[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1>O1CCCC1>[C:13]1([C:5]2([C:7]3[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=3)[C:7]3[CH:8]=[CH:9][CH:10]=[CH:11][C:12]=3[S:1](=[O:3])(=[O:2])[NH:4]2)[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

참가 물질

4

반응물 2

HCID 5143SaccharinHCID 178418255HCID 178418255, 화합물

생성물 1

HCID 46190133,3-diphenyl-2H-1,2-benzothiazole 1,1-dioxide

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

Various procedures have been reported for synthesizing 3-substituted-benz[d]isothiazole-1,1-dioxides and 3,3-disubstituted-2,3-dihydrobenz[d]isothiazole-1,1-dioxides from saccharin (3-oxo-2,3-dihydrobenz[d]isothiazole-1,1-dioxide) and from saccharin pseudo-chloride (3-chlorobenz[d]isothiazole-1,1-dioxide). As reported by A. Mustafa et al, J. Chem. Soc., 1952, p. 1339, the treatment of saccharin pseudo-chloride with excess phenylmagnesium bromide gave the corresponding 3,3-diphenyl-2,3-dihydrobenz[d]isothiazole-1,1-dioxide in almost quantitative yield. Methyl-, ethyl-, n-propyl- and n-butylmagnesium halides were reported by these authors to react analogously. R. A. Abramovitch et al, J. Chem. Soc., Perkin Trans I, 1974(22), p. 2589, reviewed and reinvestigated reagents and found that either the 3-alkyl (or 3-aryl)-benz[d]isothiazole-1,1-dioxide and/or the open-chain tertiary alcohol, o-CR2OH benzenesulfonamide wherein R is alkyl (or aryl) were obtained with one exception. When saccharin was treated with an excess of phenylmagnesium bromide in boiling tetrahydrofuran, 3,3-diphenyl-2,3-dihydrobenz[d]isothiazole-1,1-dioxide was obtained as the minor product together with the open-chain tertiary alcohol.

후처리

  1. customto react analogously
  2. customwere obtained with one exception

출처 및 근거

ORD 기록
ord-e4e2c341951b4d32a5d837eec8c8eb90
출처 데이터셋
uspto-grants-1982_01
특허 번호
US04311839

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