Triethylamine → HCID 69642450, 화합물

HRID 11430노트

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HRID 11430 반응식
[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]

참가 물질

7

반응물 4

HCID 8471TriethylamineHCID 24386Thionyl ChlorideHCID 6946556HCID 6946556, 화합물HCID 7015759(S)-1-(p-tolyl)ethanamine

생성물 1

HCID 69642450HCID 69642450, 화합물수율 71%

시약·촉매·용매 2

HCID 6228Dimethylformamide촉매HCID 6344Dichloromethane용매2회

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온도
80 °C

실험 절차

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).

후처리

  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)

출처 및 근거

ORD 기록
ord-ec579a0bb64c4ff396c5f146d1122968
출처 데이터셋
uspto-grants-2006_08
특허 번호
US07098241B2

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