Benzoic acid, 2-(chlorosulfonyl)-, methyl ester → Methyl 2-[(4-methoxypyridin-3-yl)sulfamoyl]benzoate

HRID 252212노트

반응식

HRID 252212 반응식
CO[C:3]1[CH:4]=[C:5]([NH2:9])[CH:6]=[N:7][CH:8]=1.Cl[S:11]([C:14]1[CH:23]=[CH:22][CH:21]=[CH:20][C:15]=1[C:16]([O:18][CH3:19])=[O:17])(=[O:13])=[O:12].[C:24]([O-])(O)=[O:25].[Na+]>N1C=CC=CC=1>[CH3:24][O:25][C:4]1[CH:3]=[CH:8][N:7]=[CH:6][C:5]=1[NH:9][S:11]([C:14]1[CH:23]=[CH:22][CH:21]=[CH:20][C:15]=1[C:16]([O:18][CH3:19])=[O:17])(=[O:13])=[O:12]

참가 물질

5

반응물 3

HCID 117830Benzoic acid, 2-(chlorosulfonyl)-, methyl esterHCID 516892Sodium BicarbonateHCID 127035955-Methoxypyridin-3-ylamine

생성물 1

HCID 46941843Methyl 2-[(4-methoxypyridin-3-yl)sulfamoyl]benzoate

시약·촉매·용매 1

HCID 1049Pyridine용매

실험 절차

To a solution of 5-methoxypyridin-3-amine (1 eq) in pyridine (0.4 M) was added methyl 2-(chlorosulfonyl)benzoate (1 eq) and the mixture was stirred overnight at room temperature. The mixture was diluted with saturated aqueous NaHCO3 and extracted with CH2Cl2. The organic layer was dried over Na2SO4, filtered and concentrated. The crude residue was purified by flash chromatography to give afford the title compound. 1H NMR (400 MHz, DMSO-D6) δ 9.35-9.57 (m, 1H) 8.54-8.61 (m, 1H) 8.17-8.23 (m, 1H) 7.74-7.85 (m, 2H) 7.61-7.73 (m, 1H) 7.32-7.42 (m, 1H) 6.91-7.00 (m, 1H) 3.73 (s, 3H) 3.51 (s, 3H)

후처리

  1. extractionextracted with CH2Cl2
  2. dry with materialThe organic layer was dried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe crude residue was purified by flash chromatography
  6. customto give

출처 및 근거

ORD 기록
ord-211cb20947c84e3ca7912fdc4f6f0e55
출처 데이터셋
uspto-grants-2011_01
특허 번호
US07868026B2

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