Bromide ion → 3,3-diphenyl-2H-1,2-benzothiazole 1,1-dioxide

HRID 894404

반응식

HRID 894404 반응식
[S:1]1(=[O:11])(=[O:10])[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[CH:3]=[N:2]1.S1([C:23]2[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=2)C(=O)N1)(=O)=O.[Br-]>O1CCCC1>[C:4]1([C:3]2([C:18]3[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=3)[C:4]3[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=3[S:1](=[O:10])(=[O:11])[NH:2]2)[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1

참가 물질

5

반응물 3

HCID 259Bromide ionHCID 5143SaccharinHCID 130862071H-1lambda~6~,2-Benzothiazole-1,1-dione

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 the reactions of saccharins with alkyl and aryl Grignard 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-CH2OH benzenesulfonamide wherein R is alkyl (or aryl) were obtained with one exception. When saccharin was treated with an excess of phenylmagensium 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-bbdb325dfb8447ce9cc643a9c3bc9f9c
출처 데이터셋
uspto-grants-1981_08
특허 번호
US04283537

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