4-Chlorobenzenesulfonamide → 1,1-Dimethylethyl 4-[(4-chlorophenyl)sulfonylaminocarbonyl]benzoate

HRID 1165530

反応式

HRID 1165530 の反応式
[C:1]([O:5][C:6](=[O:16])[C:7]1[CH:15]=[CH:14][C:10]([C:11]([OH:13])=O)=[CH:9][CH:8]=1)([CH3:4])([CH3:3])[CH3:2].[Cl:17][C:18]1[CH:23]=[CH:22][C:21]([S:24]([NH2:27])(=[O:26])=[O:25])=[CH:20][CH:19]=1>CN(C1C=CN=CC=1)C.C(Cl)Cl>[Cl:17][C:18]1[CH:19]=[CH:20][C:21]([S:24]([NH:27][C:11]([C:10]2[CH:9]=[CH:8][C:7]([C:6]([O:5][C:1]([CH3:2])([CH3:3])[CH3:4])=[O:16])=[CH:15][CH:14]=2)=[O:13])(=[O:25])=[O:26])=[CH:22][CH:23]=1

参加物

5

反応物 2

HCID 668244-ChlorobenzenesulfonamideHCID 27609544-(tert-Butoxycarbonyl)benzoic acid

生成物 1

HCID 545475071,1-Dimethylethyl 4-[(4-chlorophenyl)sulfonylaminocarbonyl]benzoate収率 100%

試薬・触媒・溶媒 2

HCID 142844-(Dimethylamino)pyridine触媒HCID 6344Dichloromethane溶媒2 回

実験手順

A 5-liter 3-neck round bottom flask was equipped with a mechanical stirrer and nitrogen inlet. CH2Cl2 (2 liters) was placed in the reaction flask and terephthalic acid mono-t-butyl ester (127.5 g, 0.574 mol), DMAP (70.06 g, 0.574 mol), and 4-chlorobenzenesulfonamide (110.04 g, 0.574 mol) were added in that order using CH2Cl2 (400 ml) to wash down the solids. WSCDI (110.10 g, 0.574 mol) was added in portions over 10 min using CH2Cl2 (100 ml) to wash down the solid. After the reaction mixture was stirred overnight at room temperature, it was concentrated under vacuum to dryness. The residue was partioned between EtOAc and water. The EtOAc solution was washed (20% aq citric acid, satd aq NaHCO3, brine), dried (Na2SO4), and concentrated under vacuum to a white solid. After drying in a vacuum oven at 50°, the title product (227 g, 100%) was obtained in a sufficiently pure state to be used directly for the next step; TLC, Rf =0.43, MeOH:CHCl3 (15:85). (Further purification was possible by recrystallization from EtOH:water; m.p. above 300°).

後処理

  1. customA 5-liter 3-neck round bottom flask was equipped with a mechanical stirrer and nitrogen inlet
  2. additionwere added in that order
  3. washto wash down the solids
  4. additionWSCDI (110.10 g, 0.574 mol) was added in portions over 10 min
  5. washto wash down the solid
  6. concentrationit was concentrated under vacuum to dryness
  7. washThe EtOAc solution was washed (20% aq citric acid, satd aq NaHCO3, brine)
  8. dry with materialdried (Na2SO4)
  9. concentrationconcentrated under vacuum to a white solid
  10. customAfter drying in a vacuum oven at 50°

出典と根拠

ORDレコード
ord-83d1a6e6106b4f1f88d1a06a1d75e4ea
出典データセット
uspto-grants-1990_03
特許番号
US04910190

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