Tributylamine → 1,2-Benzisothiazole, 3-chloro-5-nitro-

HRID 277375

반응식

HRID 277375 반응식
[N+:1]([C:4]1[CH:5]=[CH:6][C:7]2[S:11][NH:10][C:9](=O)[C:8]=2[CH:13]=1)([O-:3])=[O:2].P(Cl)(Cl)([Cl:16])=O.C(N(CCCC)CCCC)CCC>C(Cl)Cl>[Cl:16][C:9]1[C:8]2[CH:13]=[C:4]([N+:1]([O-:3])=[O:2])[CH:5]=[CH:6][C:7]=2[S:11][N:10]=1

참가 물질

5

반응물 3

HCID 7622TributylamineHCID 24813Phosphorus oxychlorideHCID 131869501,2-Benzisothiazol-3(2H)-one, 5-nitro-

생성물 1

HCID 1980981,2-Benzisothiazole, 3-chloro-5-nitro-

시약·촉매·용매 1

HCID 6344Dichloromethane용매

반응 조건

온도
109 °C

실험 절차

A mixture of 5-nitro-1,2-benzisothiazol-3(2H)-one (10.0 g, 0.0510 mol), phosphorus oxychloride (40.0 mL, 0.429 mol) and tributylamine (12.0 mL, 0.050 mol) is heated at 103-115° C. for six hours, stirred at room temperature overnight, and poured into an ice-water mixture. The resultant aqueous mixture is extracted with methylene chloride. The combined organic extracts are washed sequentially with water and saturated sodium hydrogen carbonate solution, dried over anhydrous sodium sulfate, and concentrated in vacuo to obtain a gum. Column chromatography of the gum using silica gel and methylene chloride gives the title product as an orange-yellow solid which is identified by NMR spectral analysis.

후처리

  1. extractionThe resultant aqueous mixture is extracted with methylene chloride
  2. washThe combined organic extracts are washed sequentially with water and saturated sodium hydrogen carbonate solution
  3. dry with materialdried over anhydrous sodium sulfate
  4. concentrationconcentrated in vacuo
  5. customto obtain a gum

출처 및 근거

ORD 기록
ord-b97e097d6d624ba4aaf28e75807e741e
출처 데이터셋
uspto-grants-2002_03
특허 번호
US06355796B1

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