Triethylamine → Methyl 2-{[(5-methylpyridin-3-yl)amino]sulfonyl}benzoate

HRID 252208

反応式

HRID 252208 の反応式
[CH3:1][C:2]1[CH:3]=[C:4]([NH2:8])[CH:5]=[N:6][CH:7]=1.C(N(CC)CC)C.Cl[S:17]([C:20]1[CH:29]=[CH:28][CH:27]=[CH:26][C:21]=1[C:22]([O:24][CH3:25])=[O:23])(=[O:19])=[O:18]>C(Cl)Cl.C([O-])(O)=O.[Na+]>[CH3:1][C:2]1[CH:3]=[C:4]([NH:8][S:17]([C:20]2[CH:29]=[CH:28][CH:27]=[CH:26][C:21]=2[C:22]([O:24][CH3:25])=[O:23])(=[O:19])=[O:18])[CH:5]=[N:6][CH:7]=1

参加物

6

反応物 3

HCID 8471TriethylamineHCID 117830Benzoic acid, 2-(chlorosulfonyl)-, methyl esterHCID 27628943-Amino-5-methylpyridine

生成物 1

HCID 58924073Methyl 2-{[(5-methylpyridin-3-yl)amino]sulfonyl}benzoate収率 34%

試薬・触媒・溶媒 2

HCID 6344Dichloromethane溶媒HCID 516892Sodium Bicarbonate溶媒

実験手順

To a solution of 5-methylpyridin-3-amine (0.5 g, 4.62 mmol) in CH2Cl2 (50 ml) were added triethylamine (0.64 mL, 4.62 mmol) and methyl 2-(chlorosulfonyl)benzoate (1.08 g, 4.62 mmol). The resulting mixture was stirred at room temperature for 1 hour. The mixture was then 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 (0-8% MeOH/CH2Cl2) to give the title compound (0.476 g, 34%). 1H NMR (400 MHz, DMSO-D6) δ ppm 10.25-10.62 (m, 1H) 8.6 (s, 2H) 7.81-7.93 (m, 1H) 7.64-7.76 (m, 2H) 7.54-7.64 (m, 1H) 7.28 (s, 1H) 3.80 (s, 3H) 2.18 (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 (0-8% MeOH/CH2Cl2)

出典と根拠

ORDレコード
ord-6f001939915e4bf99a8728db4c5e78d8
出典データセット
uspto-grants-2011_01
特許番号
US07868026B2

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