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

HRID 1709980

反応式

HRID 1709980 の反応式
[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]

参加物

6

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 180Acetone溶媒HCID 962Water溶媒2 回

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-13a5a5f03c734c9d991617993ffc4ea6
出典データセット
uspto-grants-1990_08
特許番号
US04952573

関連ノート

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