Ethyl Acetate → 2-(3,3-diethoxypropyl)-3,4-dihydro-2-(3,4-dimethoxyphenyl)-4-methyl-3-oxo-2H-1,4-benzothiazine

HRID 649330

反応式

HRID 649330 の反応式
[H-].[Na+].[CH3:3][O:4][C:5]1[CH:6]=[C:7]([CH:13]2[C:18](=[O:19])[N:17]([CH3:20])[C:16]3[CH:21]=[CH:22][CH:23]=[CH:24][C:15]=3[S:14]2)[CH:8]=[CH:9][C:10]=1[O:11][CH3:12].[CH2:25]([O:27][CH:28]([O:32][CH2:33][CH3:34])[CH2:29][CH2:30]Cl)[CH3:26].C(OCC)(=O)C>CN(C)C=O.O>[CH2:25]([O:27][CH:28]([O:32][CH2:33][CH3:34])[CH2:29][CH2:30][C:13]1([C:7]2[CH:8]=[CH:9][C:10]([O:11][CH3:12])=[C:5]([O:4][CH3:3])[CH:6]=2)[C:18](=[O:19])[N:17]([CH3:20])[C:16]2[CH:21]=[CH:22][CH:23]=[CH:24][C:15]=2[S:14]1)[CH3:26]

参加物

7

反応物 4

HCID 8857Ethyl AcetateHCID 24758Sodium hydrideHCID 962173-Chloro-1,1-diethoxypropaneHCID 14244692HCID 14244692、化合物

生成物 1

HCID 201430342-(3,3-diethoxypropyl)-3,4-dihydro-2-(3,4-dimethoxyphenyl)-4-methyl-3-oxo-2H-1,4-benzothiazine収率 71.5%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6228Dimethylformamide溶媒2 回

実験手順

To a stirred suspension of 60% sodium hydride (0.6 g) in dimethylformamide (5 ml), 3,4-dihydro-2-(3,4-dimethoxyphenyl)-4-methyl-3-oxo-2H-1,4-benzothiazine (4.4 g) dissolved in dimethylformamide (15 ml) is added under nitrogen atmosphere and ice-cooling, and the mixture is stirred for 15 minutes at room temperature. β-Chloropropionaldehyde diethyl acetal (2.8 g) is added to the reaction mixture, and the mixture is stirred for 2.5 hours at 60° C. The mixture is poured into a mixture of ethyl acetate and water. The organic layer is washed with 1N sodium hydroxide and saturated aqueous sodium chloride solution, dried over anhydrous sodium sulfate and concentrated in vacuo. The residue is purified by silica gel column chromatography to give 4.4 g (71.5 %) of 2-(3,3-diethoxypropyl)-3,4-dihydro-2-(3,4-dimethoxyphenyl)-4-methyl-3-oxo-2H-1,4-benzothiazine as an oily form (compound No. 36, (IR: neat, cm-1) 1660, 1588, 1444, 1325, 1238, 750).

後処理

  1. additionis added under nitrogen atmosphere
  2. temperatureice-cooling
  3. stirringthe mixture is stirred for 2.5 hours at 60° C
  4. washThe organic layer is washed with 1N sodium hydroxide and saturated aqueous sodium chloride solution
  5. dry with materialdried over anhydrous sodium sulfate
  6. concentrationconcentrated in vacuo
  7. customThe residue is purified by silica gel column chromatography

出典と根拠

ORDレコード
ord-ad637bf96dca4005bd7f8a8efee8d099
出典データセット
uspto-grants-1988_04
特許番号
US04739050

関連ノート

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