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

HRID 974372Notes

Reaction equation

HRID 974372 reaction equation
[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]

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 24386Thionyl ChlorideHCID 865772-(Ethoxycarbonyl)cyclohexane-1-carboxylic acidHCID 132729265-Allyloxy-4-chloro-2-fluoroaniline

Product 1

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

Reagents, catalysts & solvents 3

HCID 1049PyridineSolventHCID 6344DichloromethaneSolventHCID 8471TriethylamineSolvent

Procedure

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.

Workup

  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))

Sources & evidence

ORD record
ord-b4793f4dcc694ffaaa8716244c6ab6e2
Source dataset
uspto-grants-1991_11
Patent number
US05068365

Reaction notes

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