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

HRID 1199680

反応式

HRID 1199680 の反応式
[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

参加物

4

反応物 2

HCID 179093-Chlorobenzenesulphonyl chlorideHCID 14989640HCID 14989640、化合物

生成物 1

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

試薬・触媒・溶媒 1

HCID 1049Pyridine溶媒2 回

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-a7a6c8655a0a442a8086d27148a0f556
出典データセット
uspto-grants-1990_02
特許番号
US04902698

関連ノート

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