N-(2-aminophenyl)-4-chlorobenzenesulfonamide → Benzofuran-2-sulfonic acid [2-(4-chlorobenzenesulfonylamino)phenyl]-amide

HRID 730215노트

반응식

HRID 730215 반응식
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[NH:8][S:9]([C:12]1[CH:17]=[CH:16][C:15]([Cl:18])=[CH:14][CH:13]=1)(=[O:11])=[O:10].[O:19]1[C:23]2[CH:24]=[CH:25][CH:26]=[CH:27][C:22]=2[CH:21]=[C:20]1[S:28](Cl)(=[O:30])=[O:29]>C(Cl)Cl.N1C=CC=CC=1>[Cl:18][C:15]1[CH:14]=[CH:13][C:12]([S:9]([NH:8][C:3]2[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=2[NH:1][S:28]([C:20]2[O:19][C:23]3[CH:24]=[CH:25][CH:26]=[CH:27][C:22]=3[CH:21]=2)(=[O:29])=[O:30])(=[O:11])=[O:10])=[CH:17][CH:16]=1

참가 물질

5

반응물 2

HCID 241359N-(2-aminophenyl)-4-chlorobenzenesulfonamideHCID 27951721-Benzofuran-2-sulfonyl chloride

생성물 1

HCID 11626794Benzofuran-2-sulfonic acid [2-(4-chlorobenzenesulfonylamino)phenyl]-amide수율 39.7%

시약·촉매·용매 2

HCID 1049Pyridine용매HCID 6344Dichloromethane용매2회

실험 절차

To a solution of N-(2-aminophenyl)-4-chlorobenzenesulfonamide (0.5 mmol, prepared as in Example 11) in DCM (1 mL) and pyridine (1 mL), benzofuran-2-sulfonyl chloride (0.55 mmol), prepared as above, was added at RT and the reaction mixture was then allowed to stir at RT overnight or until the reaction was complete as determined by TLC or LC-MS. The reaction mixture was then diluted with DCM (5 mL). The organic phase was washed with 10% aqueous HCl (5 mL), water (5 mL) and brine (5 mL). The organic phase was dried over anhydrous sodium sulfate, and concentrated under vacuum. The residue obtained was purified by flash column chromatography eluting with DCM/EtOAc to afford 92 mg benzofuran-2-sulfonic acid [2-(4-chlorobenzenesulfonylamino)phenyl]-amide. LC: Tr 1.13 min, MS: 464.0 (M+1)+.

후처리

  1. additionwas added at RT
  2. washThe organic phase was washed with 10% aqueous HCl (5 mL), water (5 mL) and brine (5 mL)
  3. dry with materialThe organic phase was dried over anhydrous sodium sulfate
  4. concentrationconcentrated under vacuum
  5. customThe residue obtained
  6. customwas purified by flash column chromatography
  7. washeluting with DCM/EtOAc

출처 및 근거

ORD 기록
ord-a53d164d5b274e2cae64dbc418cb38d9
출처 데이터셋
uspto-grants-2009_09
특허 번호
US07582673B2

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