Ethyl 2-aminobenzoate → 2-[(Ethoxycarbonyl)amino]benzoic acid ethyl ester

HRID 1709980

반응식

HRID 1709980 반응식
[CH2:1]([O:3][C:4](=[O:12])[C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[NH2:11])[CH3:2].C(=O)([O-])[O-].[K+].[K+].Cl[C:20]([O:22][CH2:23][CH3:24])=[O:21]>CC(C)=O.O>[CH2:1]([O:3][C:4](=[O:12])[C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[NH:11][C:20]([O:22][CH2:23][CH3:24])=[O:21])[CH3:2]

참가 물질

6

반응물 3

HCID 6877Ethyl 2-aminobenzoateHCID 10928Ethyl chloroformateHCID 11430Potassium Carbonate

생성물 1

HCID 41533612-[(Ethoxycarbonyl)amino]benzoic acid ethyl ester수율 98.4%

시약·촉매·용매 2

HCID 180Acetone용매HCID 962Water용매2회

실험 절차

To an ice cooled solution of ethyl-o-aminobenzoate 1 (33 g, 0.2 mole) in acetone (270 ml) was added with stirring an ice cooled solution of potassium carbonate (36.7 g, 0.27 mole) in water (214 ml) followed by addition of ethyl chloroformate (43 g, 0.4 mole). Stirring was continued at 0° C. for 11/2 hour and at 25° C. for 2 hours. The mixture was poured in water (300 ml) and extracted with three 300 ml portions of ether. The combined and dried (MgSO4) ether phases were evaporated in vacuo to give pure 2 (46.7 g, 98%). The product was recrystallized (EtOH, H2O) to give colorless crystals, mp <40° C. (Calc. for C12H15NO4 : C 60.75; H 6.37; N 5.90). (Found C 60.75; H 6.29; N 5.85) 1H NMR (CDCl3) δ= 1.3 (3H, t, J=7 Hz) 1.4 (3H, t, J=7 Hz) 4.2 (2H, q, J=7 Hz) 4.3 (2H, q, J=7 Hz) 6.9-8.5 (4H, AA'BB'). IR (CCl4): 3300(m), 2980(m), 1735(s), 1690(s), 1600(s), 1510(w), 1450(s).

후처리

  1. customwas continued at 0° C. for 11
  2. custom2 hour
  3. extractionextracted with three 300 ml portions of ether
  4. dry with materialdried (MgSO4) ether phases
  5. customwere evaporated in vacuo

출처 및 근거

ORD 기록
ord-13a5a5f03c734c9d991617993ffc4ea6
출처 데이터셋
uspto-grants-1990_08
특허 번호
US04952573

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