Triethylamine → HCID 69642450、化合物

HRID 11430ノート

反応式

HRID 11430 の反応式
[S:1]1[C:5]([C:6]([O-:8])=O)=[CH:4][CH:3]=[C:2]1[C:9]([O:11][CH3:12])=[O:10].S(Cl)(Cl)=O.[C:17]1([CH3:26])[CH:22]=[CH:21][C:20]([C@@H:23]([NH2:25])[CH3:24])=[CH:19][CH:18]=1.C(N(CC)CC)C>C(Cl)Cl.CN(C=O)C>[CH3:12][O:11][C:9]([C:2]1[S:1][C:5]([C:6](=[O:8])[NH:25][C@H:23]([C:20]2[CH:21]=[CH:22][C:17]([CH3:26])=[CH:18][CH:19]=2)[CH3:24])=[CH:4][CH:3]=1)=[O:10]

参加物

7

反応物 4

HCID 8471TriethylamineHCID 24386Thionyl ChlorideHCID 6946556HCID 6946556、化合物HCID 7015759(S)-1-(p-tolyl)ethanamine

生成物 1

HCID 69642450HCID 69642450、化合物収率 71%

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide触媒HCID 6344Dichloromethane溶媒2 回

反応条件

温度
80 °C

実験手順

A solution of 1.4 g (7.5 mmol) of methyl thiophen-2,5-dicarboxylate in CH2Cl2 (5 ml) is treated with 1.5 ml (18 mmol) thionylchloride and one drop of DMF and subsequently heated at 80° C. for 1 hour. The solvent and excess of thionylchloride are evaporated under reduced pressure, and the residue is dissolved in CH2Cl2 (10 ml) and treated slowly with (S)-1-(p-tolyl)ethylamine (1.0 g, 7.4 mmol) in CH2Cl2 (10 ml) and triethylamin (2 ml, 14.2 mmol). Stirring at rt is continued for 1 additional hour. The product is isolated after acidic work-up and recrystallisation as yellow solid (mp=165° C.) in 71% yield (1.6 g).

後処理

  1. customThe solvent and excess of thionylchloride are evaporated under reduced pressure
  2. dissolutionthe residue is dissolved in CH2Cl2 (10 ml)
  3. customThe product is isolated
  4. customafter acidic work-up and recrystallisation as yellow solid (mp=165° C.) in 71% yield (1.6 g)

出典と根拠

ORDレコード
ord-ec579a0bb64c4ff396c5f146d1122968
出典データセット
uspto-grants-2006_08
特許番号
US07098241B2

反応ノート

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