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

HRID 1165530

반응식

HRID 1165530 반응식
[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

참가 물질

5

반응물 2

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

생성물 1

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

시약·촉매·용매 2

HCID 142844-(Dimethylamino)pyridine촉매HCID 6344Dichloromethane용매2회

실험 절차

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°).

후처리

  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°

출처 및 근거

ORD 기록
ord-83d1a6e6106b4f1f88d1a06a1d75e4ea
출처 데이터셋
uspto-grants-1990_03
특허 번호
US04910190

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