Benzaldehyde → Ethyl 2-(benzylideneamino)acetate

HRID 1445956

반응식

HRID 1445956 반응식
Cl.[CH2:2]([O:4][C:5](=[O:14])[CH2:6][NH:7]C1C=CC=CC=1)[CH3:3].[CH:15](=O)[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.S([O-])([O-])(=O)=O.[Mg+2].C(N(CC)CC)C>O.C(OCC)C.ClCCl>[C:16]1([CH:15]=[N:7][CH2:6][C:5]([O:4][CH2:2][CH3:3])=[O:14])[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

참가 물질

8

반응물 4

HCID 240BenzaldehydeHCID 8471TriethylamineHCID 24083Sulfuric acid magnesium salt (1:1)HCID 12241367Ethyl N-phenylglycinate hydrochloride

생성물 1

HCID 357745Ethyl 2-(benzylideneamino)acetate수율 131.8%

시약·촉매·용매 3

HCID 962Water용매HCID 3283Diethyl Ether용매HCID 6344Dichloromethane용매

실험 절차

To a mixture of 10.6 g of ethyl phenylglycinate hydrochloride 2 (49.3 mmol), 100 mL of dichloromethane, 5 ml of benzaldehyde (49.2 mmol) and 30 g of magnesium sulfate (249.2 mmol) were added at room temperature, under a nitrogen atmosphere, 21.25 mL of triethylamine (152.46 mmol). After stirring for 17 h the heterogeneous reaction mixture was filtered through celite and the solid was washed with 100 mL of dichloromethane. The solvents were evaporated under reduced pressure and the viscous oil thus obtained was stirred with 80 mL of diethyl ether and 80 mL of water until dissolution. After decantation, the organic layer was dried over sodium sulphate and the solvent was evaporated under vacuum. The immine ester 3 (12.4 g, 94% yield) was obtained as a yellow pale oil.

후처리

  1. additionwere added at room temperature, under a nitrogen atmosphere
  2. filtrationwas filtered through celite
  3. washthe solid was washed with 100 mL of dichloromethane
  4. customThe solvents were evaporated under reduced pressure
  5. customthe viscous oil thus obtained
  6. dry with materialAfter decantation, the organic layer was dried over sodium sulphate
  7. customthe solvent was evaporated under vacuum

출처 및 근거

ORD 기록
ord-f913aea34d7d47dca9e591881e907db7
출처 데이터셋
uspto-grants-2010_02
특허 번호
US07666907B2

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