Triethylamine → N-(4-Methoxybenzylidene)glycine methyl ester

HRID 722446노트

반응식

HRID 722446 반응식
Cl.[CH3:2][O:3][C:4](=[O:7])[CH2:5][NH2:6].C(N(CC)CC)C.[CH:15](=O)[C:16]1[CH:21]=[CH:20][C:19]([O:22][CH3:23])=[CH:18][CH:17]=1.[O-]S([O-])(=O)=O.[Mg+2]>C(Cl)Cl>[CH3:2][O:3][C:4](=[O:7])[CH2:5][N:6]=[CH:15][C:16]1[CH:21]=[CH:20][C:19]([O:22][CH3:23])=[CH:18][CH:17]=1

참가 물질

6

반응물 4

HCID 8471TriethylamineHCID 24083Sulfuric acid magnesium salt (1:1)HCID 312444-MethoxybenzaldehydeHCID 122755Glycine methyl ester hydrochloride

생성물 1

HCID 4193973N-(4-Methoxybenzylidene)glycine methyl ester수율 100.1%

시약·촉매·용매 1

HCID 6344Dichloromethane용매2회

실험 절차

To a solution of 77.46 g (0.617 mol) of glycine methylester hydrochloride in CH2Cl2, 92 ml (0.66 mol) of triethylamine, a solution of 60 g (0.44 mol) of p-anisaldehyde in 50 ml of CH2Cl2 and 40 g of MgSO4 are successively added at 0–5° C. under N2 atmosphere. After stirring for 18 h at r.t. the reaction mixture is filtered through celite and washed with CH2Cl2. The filtrate is concentrated under reduced pressure and then the crude mixture is diluted with AcOEt. The AcOEt solution is filtered again to remove triethylamine hydrochloride and the filtrate diluted with toluene and concentrated under reduced pressure (azeotropic removal of H2O) to give 91.3 g of [(4-methoxy-benzylidene)-amino]-acetic acid methyl ester as light yellow crystals; NMR (C6D6): 3.18 (s, 3H), 3.34 (s, 3H), 4.13 (s, 3H), 6.69 (d, 2H, J=8.56 Hz), 7.70 (d, 2H, J=8.56 Hz), 7.79 (s, 1H).

후처리

  1. filtrationis filtered through celite
  2. washwashed with CH2Cl2
  3. concentrationThe filtrate is concentrated under reduced pressure
  4. additionthe crude mixture is diluted with AcOEt
  5. filtrationThe AcOEt solution is filtered again
  6. customto remove triethylamine hydrochloride
  7. additionthe filtrate diluted with toluene
  8. concentrationconcentrated under reduced pressure (azeotropic removal of H2O)

출처 및 근거

ORD 기록
ord-68500bfdae52498db5d9c33bfab0e7a5
출처 데이터셋
uspto-grants-2006_11
특허 번호
US07138432B1

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