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

HRID 252212ノート

反応式

HRID 252212 の反応式
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]

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 1049Pyridine溶媒

実験手順

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)

後処理

  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

出典と根拠

ORDレコード
ord-211cb20947c84e3ca7912fdc4f6f0e55
出典データセット
uspto-grants-2011_01
特許番号
US07868026B2

反応ノート

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