2-Chloroaniline → 3-(2-Chlorophenyl)-2-(2-ethylcarbamoylethyl)-5,7-dimethyl-4-oxo-3,4-dihydroquinazoline-6-carboxylic Acid Ethyl Ester

HRID 1039366노트

반응식

HRID 1039366 반응식
[CH2:1]([O:3][C:4]([C:6]1[C:7]([CH3:32])=[C:8]2[C:13](=[CH:14][C:15]=1[CH3:16])[N:12]=[C:11]([CH2:17][CH2:18][C:19]([O:21]CC)=O)[N:10]([C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=1[Cl:30])[C:9]2=[O:31])=[O:5])[CH3:2].C(OC(=O)C1C(C)=C[C:43]([NH:47]C(=O)CCC(OCC)=O)=[C:39](C(O)=O)C=1C)C.ClC1C=CC=CC=1N.P(Cl)(Cl)Cl.C(=O)([O-])O.[Na+]>C1(C)C=CC=CC=1>[CH2:1]([O:3][C:4]([C:6]1[C:7]([CH3:32])=[C:8]2[C:13](=[CH:14][C:15]=1[CH3:16])[N:12]=[C:11]([CH2:17][CH2:18][C:19](=[O:21])[NH:47][CH2:43][CH3:39])[N:10]([C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=1[Cl:30])[C:9]2=[O:31])=[O:5])[CH3:2]

참가 물질

7

반응물 5

HCID 72402-ChloroanilineHCID 24387Phosphorus trichlorideHCID 516892Sodium BicarbonateHCID 671755223-(2-Chlorophenyl)-2-(2-ethoxycarbonylethyl)-5,7-dimethyl-4-oxo-3,4-dihydroquinazoline-6-carboxylic acid ethyl esterHCID 865975834-(3-Ethoxycarbonylpropionylamino)-2,6-dimethylisophthalic acid 1-ethyl ester

생성물 1

HCID 115906083-(2-Chlorophenyl)-2-(2-ethylcarbamoylethyl)-5,7-dimethyl-4-oxo-3,4-dihydroquinazoline-6-carboxylic Acid Ethyl Ester

시약·촉매·용매 1

HCID 1140Toluene용매

반응 조건

온도
130 °C

실험 절차

3-(2-Chlorophenyl)-2-(2-ethoxycarbonylethyl)-5,7-dimethyl-4-oxo-3,4-dihydroquinazoline-6-carboxylic acid ethyl ester: A stirred mixture of 4-(3-ethoxycarbonylpropionylamino)-2,6-dimethylisophthalic acid 1-ethyl ester (0.327 g, 0.89 mmol), 2-chloroaniline (0.28 mL, 2.66 mmol) and phosphorus trichloride (0.74 g, 5.4 mmol) in toluene (6 mL) is heated at 130° C. for 3 h. Upon cooling to room temperature, the reaction mixture is poured onto saturated sodium hydrogen carbonate solution and extracted with chloroform. The chloroform extracts are combined, washed with brine and dried over anhydrous MgSO4. The solvent is removed under reduced pressure and the residue is purified by flash chromatography over silica gel (initial eluent: 19:1 cyclohexane:ethyl acetate; final eluent: 7:3 cyclohexane:ethyl acetate) to afford the title compound.

후처리

  1. temperatureUpon cooling to room temperature
  2. extractionextracted with chloroform
  3. washwashed with brine
  4. dry with materialdried over anhydrous MgSO4
  5. customThe solvent is removed under reduced pressure
  6. customthe residue is purified by flash chromatography over silica gel (initial eluent: 19:1 cyclohexane:ethyl acetate; final eluent: 7:3 cyclohexane:ethyl acetate)

출처 및 근거

ORD 기록
ord-00f1168618d54f7ea38050658f656957
출처 데이터셋
uspto-grants-2013_10
특허 번호
US08552015B2

반응 노트

불러오는 중…