N-Acetylsulfanilyl chloride → Methyl 2-{[2-({[4-(acetylamino)phenyl]sulfonyl}amino)phenyl]thio}benzoate

HRID 746741

반응식

HRID 746741 반응식
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[S:8][C:9]1[CH:18]=[CH:17][CH:16]=[CH:15][C:10]=1[C:11]([O:13][CH3:14])=[O:12].[C:19]([NH:22][C:23]1[CH:28]=[CH:27][C:26]([S:29](Cl)(=[O:31])=[O:30])=[CH:25][CH:24]=1)(=[O:21])[CH3:20]>N1C=CC=CC=1.C(OCC)(=O)C>[C:19]([NH:22][C:23]1[CH:24]=[CH:25][C:26]([S:29]([NH:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=2[S:8][C:9]2[CH:18]=[CH:17][CH:16]=[CH:15][C:10]=2[C:11]([O:13][CH3:14])=[O:12])(=[O:31])=[O:30])=[CH:27][CH:28]=1)(=[O:21])[CH3:20]

참가 물질

5

반응물 2

HCID 8481N-Acetylsulfanilyl chlorideHCID 614949Methyl 2-[(2-aminophenyl)sulfanyl]benzoate

생성물 1

HCID 11442458Methyl 2-{[2-({[4-(acetylamino)phenyl]sulfonyl}amino)phenyl]thio}benzoate

시약·촉매·용매 2

HCID 1049Pyridine용매HCID 8857Ethyl Acetate용매

실험 절차

A solution of methyl 2-[(2-aminophenyl)thio]benzoate (0.444 g, 1.71 mmol) and 4-(acetylamino)benzenesulfonyl chloride (0.440 g, 1.88 mmol) in pyridine (1.6 mL) was stirred at room temperature for 1 hr. The reaction mixture was diluted with ethyl acetate and washed with 0.5 N HCl (×2), water (×2), half brine and brine. The organic layer was dried over sodium sulfate, filtered, and concentrated. The residue was purified by silica gel chromatography eluted with 1-5% MeOH in DCM to provide the title compound. MS (ES, M+H+): 457.2. 1H NMR (400 MHz, CD3OD) δ 7.92 (bd, J=8 Hz, 1H), 7.75 (bd, J=8 Hz, 1H), 7.55 (bd, J=9.2 Hz, 2H), 7.50-7.44 (m, 3H), 7.42 (bd, J=8 Hz, 1H), 7.18 (bt, J=7.6 Hz, 1H), 7.14 (bt, J=7.6 Hz, 1H), 7.05 (bt, J=8 Hz, 1H), 6.23 (bd, J=8 Hz, 1H), 3.95 (s, 3H), 2.14 (s, 3).

후처리

  1. washwashed with 0.5 N HCl (×2), water (×2), half brine and brine
  2. dry with materialThe organic layer was dried over sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe residue was purified by silica gel chromatography
  6. washeluted with 1-5% MeOH in DCM

출처 및 근거

ORD 기록
ord-02c64c4ec5bc4132bdd771d93dd44e68
출처 데이터셋
uspto-grants-2008_07
특허 번호
US07393873B2

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