Ammonia → 3-Chloropyridine-2-sulfonamide

HRID 1154531노트

반응식

HRID 1154531 반응식
Cl[C:2]1[C:7]([Cl:8])=[CH:6][CH:5]=[CH:4][N:3]=1.ClCl.[S:11](Cl)(Cl)(=[O:13])=[O:12].[NH3:16]>C(S)C1C=CC=CC=1.CN(C)C=O.CS(C)=O>[Cl:8][C:7]1[C:2]([S:11]([NH2:16])(=[O:13])=[O:12])=[N:3][CH:4]=[CH:5][CH:6]=1

참가 물질

8

반응물 4

HCID 222AmmoniaHCID 169882,3-DichloropyridineHCID 24526ChlorineHCID 24648Sulfuryl chloride

생성물 1

HCID 146531913-Chloropyridine-2-sulfonamide

시약·촉매·용매 3

HCID 679Dimethyl Sulfoxide용매HCID 6228Dimethylformamide용매HCID 7509Benzyl mercaptan용매

실험 절차

The halopyridine sulfonamide of the present invention is prepared in a two-step process. In step one, benzyl mercaptan is dissolved in a solvent such as dimethylformamide or dimethylsulfoxide, mixed with 2,3-dichloropyridine and heated at about 50°-100° C. for about 2-6 hours. The residue is taken up in a solvent and distilled to give the resulting product, 3-chloro-2-(phenylmethyl)thio)pyridine. In step two, the halophenylmethylthiopyridine prepared in step one is converted by oxidative chlorination to a halopyridine sulfonyl chloride upon exposure to chlorine. The resulting sulfonyl chloride compound is reacted with aqueous ammonia for about 16 hours. The mixture is then acidified to a pH of about 5 and extracted with a suitable solvent, preferably ethyl acetate, and dried for 3-5 hours to yield the novel product, 3-chloro-2-pyridine sulfonamide. The product of the present invention is a colorless, needle-like, crystalline solid with a melting point of 128°-130° C. It is soluble in the usual organic solvents and in warm water.

후처리

  1. temperatureheated at about 50°-100° C. for about 2-6 hours
  2. distillationdistilled
  3. customto give the resulting product, 3-chloro-2-(phenylmethyl)thio)pyridine
  4. extractionextracted with a suitable solvent, preferably ethyl acetate
  5. customdried for 3-5 hours

출처 및 근거

ORD 기록
ord-b81ee8c76b5f4f5299cb6fbd8c9087c2
출처 데이터셋
uspto-grants-1984_12
특허 번호
US04490380

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