3-Chlorobenzenesulphonyl chloride → 4-[5-(3-Chlorobenzenesulphonamido)pyrid-2-yl]butanoic acid

HRID 1199680

반응식

HRID 1199680 반응식
[Cl:1][C:2]1[CH:3]=[C:4]([S:8](Cl)(=[O:10])=[O:9])[CH:5]=[CH:6][CH:7]=1.[NH2:12][C:13]1[CH:14]=[CH:15][C:16]([CH2:19][CH2:20][CH2:21][C:22]([OH:24])=[O:23])=[N:17][CH:18]=1>N1C=CC=CC=1>[Cl:1][C:2]1[CH:3]=[C:4]([S:8]([NH:12][C:13]2[CH:14]=[CH:15][C:16]([CH2:19][CH2:20][CH2:21][C:22]([OH:24])=[O:23])=[N:17][CH:18]=2)(=[O:10])=[O:9])[CH:5]=[CH:6][CH:7]=1

참가 물질

4

반응물 2

HCID 179093-Chlorobenzenesulphonyl chlorideHCID 14989640HCID 14989640, 화합물

생성물 1

HCID 198654884-[5-(3-Chlorobenzenesulphonamido)pyrid-2-yl]butanoic acid수율 65.6%

시약·촉매·용매 1

HCID 1049Pyridine용매2회

실험 절차

A solution of 3-chlorobenzenesulphonyl chloride (1.17 g), dissolved in 5 ml pyridine, was added dropwise to a solution of 4-(5-aminopyrid-2-yl)butanoic acid (1 g) in pyridine (10 ml). The resulting solution was allowed to stand at room temperature overnight when the solvent was removed under reduced pressure. The residue was taken up in dilute sodium hydroxide solution (40 ml) and extracted with chloroform (4×50 ml) the chloroform extracts were discarded. The aqueous layer was adjusted to pH 4 with hydrochloric acid, extracted with chloroform (3×100 ml) and then ethyl acetate (2×100 ml). Chloroform and ethyl acetate extracts were dried over magnesium sulphate, solvents removed and residue recrystallised from acetonitrile/water to give the title compound (1.29 g) as a white solid. m.p. 141°-142° C.

후처리

  1. customwhen the solvent was removed under reduced pressure
  2. extractionextracted with chloroform (4×50 ml) the chloroform extracts
  3. extractionextracted with chloroform (3×100 ml)
  4. dry with materialChloroform and ethyl acetate extracts were dried over magnesium sulphate, solvents
  5. customremoved
  6. customresidue recrystallised from acetonitrile/water

출처 및 근거

ORD 기록
ord-a7a6c8655a0a442a8086d27148a0f556
출처 데이터셋
uspto-grants-1990_02
특허 번호
US04902698

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