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

HRID 974372ノート

反応式

HRID 974372 の反応式
[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]

参加物

8

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 3

HCID 1049Pyridine溶媒HCID 6344Dichloromethane溶媒HCID 8471Triethylamine溶媒

実験手順

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.

後処理

  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))

出典と根拠

ORDレコード
ord-b4793f4dcc694ffaaa8716244c6ab6e2
出典データセット
uspto-grants-1991_11
特許番号
US05068365

反応ノート

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