Triethylamine → HCID 35177757、化合物

HRID 1049960ノート

反応式

HRID 1049960 の反応式
CS[C:3]([S:13][CH3:14])=[C:4]([C:10](=O)[CH3:11])[C:5]([O:7][CH2:8][CH3:9])=[O:6].C(O)(=O)C.[C:19]([NH2:27])(=[NH:26])[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1.C(N(CC)CC)C>C(O)C>[CH3:11][C:10]1[C:4]([C:5]([O:7][CH2:8][CH3:9])=[O:6])=[C:3]([S:13][CH3:14])[N:27]=[C:19]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[N:26]=1

参加物

5

反応物 3

HCID 8471TriethylamineHCID 4997384Butanoic acid, 2-[bis(methylthio)methylene]-3-oxo-, ethyl esterHCID 12238987Benzenecarboximidamide, monoacetate

生成物 1

HCID 35177757HCID 35177757、化合物収率 60.7%

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

実験手順

To a solution of ethyl 2-(bis(methylthio)methylene)-3-oxobutanoate (500 mg, 2 mmol) in ethanol was added benzamidine acetate (732 mg, 6 mmol) and triethyl amine (1.41 mL) and the reaction mixture was refluxed overnight. The reaction mixture was concentrated and partitioned between ethyl acetate and water and the organic layer washed with water and dried over Na2SO4 and the solvent evaporated in vacuum. The crude product was purified by column chromatography over silica gel using 1% ethyl acetate in petroleum ether as eluent to give the desired product (350 mg). 1H-NMR 400 Hz (CDCl3): δ 8.50 (d, J=7.6 Hz, 2H), 7.50-7.46 (m, 3H), 4.45 (q, J=7.2 Hz, 2H), 2.67 (s, 3H), 2.65 (s, 3H), 1.44 (t, J=7.2 Hz, 3H); MS m/z 288.7 (M+1).

後処理

  1. temperaturethe reaction mixture was refluxed overnight
  2. concentrationThe reaction mixture was concentrated
  3. custompartitioned between ethyl acetate and water
  4. washthe organic layer washed with water
  5. dry with materialdried over Na2SO4
  6. customthe solvent evaporated in vacuum
  7. customThe crude product was purified by column chromatography over silica gel using 1% ethyl acetate in petroleum ether as eluent

出典と根拠

ORDレコード
ord-7cc380c8dd94472d8ddbc567fbf4f0ef
出典データセット
uspto-grants-2016_07
特許番号
US09382277B2

反応ノート

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