Hydrochloric Acid → N-(5-allyloxy-4-chloro-2-fluorophenyl)-2-ethoxycarbonyl cyclohexyl carboxylic amide

HRID 974372노트

반응식

HRID 974372 반응식
[CH2:1]([O:3][C:4](=[O:14])[CH:5]1[CH2:13][CH2:12][CH2:11][CH2:10][CH:6]1[C:7]([OH:9])=O)[CH3:2].S(Cl)(Cl)=O.[CH2:19]([O:22][C:23]1[C:24]([Cl:31])=[CH:25][C:26]([F:30])=[C:27]([CH:29]=1)[NH2:28])[CH:20]=[CH2:21].Cl>C(Cl)Cl.C(N(CC)CC)C.N1C=CC=CC=1>[CH2:19]([O:22][C:23]1[C:24]([Cl:31])=[CH:25][C:26]([F:30])=[C:27]([NH:28][C:7]([CH:6]2[CH2:10][CH2:11][CH2:12][CH2:13][CH:5]2[C:4]([O:3][CH2:1][CH3:2])=[O:14])=[O:9])[CH:29]=1)[CH:20]=[CH2:21]

참가 물질

8

반응물 4

HCID 313Hydrochloric AcidHCID 24386Thionyl ChlorideHCID 86577Monoethyl cyclohexane-1,2-dicarboxylateHCID 132729265-Allyloxy-4-chloro-2-fluoroaniline

생성물 1

HCID 14517279N-(5-allyloxy-4-chloro-2-fluorophenyl)-2-ethoxycarbonyl cyclohexyl carboxylic amide

시약·촉매·용매 3

HCID 1049Pyridine용매HCID 6344Dichloromethane용매HCID 8471Triethylamine용매

실험 절차

In 20 ml of methylene chloride, 1.20 g of 1,2,3,4,5,6-hexahydrophthalic acid monoethyl ester was dissolved. To this solution 0.47 g of pyridine and 0.71 g of thionyl chloride were added and the resulting mixture was stirred at room temperature. Two hour later, 1 20 g of 5-allyloxy-4-chloro-2-fluoroaniline and 0.61 g of triethylamine were added and the resulting mixture was stirred at room temperature for 5 hours. After completion of the reaction, 10% hydrochloric acid was added to the reaction mixture to make the same acidic and was extracted twice with methylene chloride. The extract was washed with saturated aqueous sodium hydrogen carbonate and dried over magnesium sulfate. The solvent was evaporated under reduced pressure and the residue was purified by column chromatography (silica gel, hexane/ethyl acetate =5/1 (v/v)) to obtain 1.5 g of light brown crystal.

후처리

  1. stirringthe resulting mixture was stirred at room temperature for 5 hours
  2. additionwas added to the reaction mixture
  3. extractionwas extracted twice with methylene chloride
  4. washThe extract was washed with saturated aqueous sodium hydrogen carbonate
  5. dry with materialdried over magnesium sulfate
  6. customThe solvent was evaporated under reduced pressure
  7. customthe residue was purified by column chromatography (silica gel, hexane/ethyl acetate =5/1 (v/v))

출처 및 근거

ORD 기록
ord-b4793f4dcc694ffaaa8716244c6ab6e2
출처 데이터셋
uspto-grants-1991_11
특허 번호
US05068365

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