2,5-Dimethoxyaniline → N-(2,5-dimethoxyphenyl)cyclohexanecarboxamide

HRID 1179116Notes

Reaction equation

HRID 1179116 reaction equation
[CH:1]1([C:7](Cl)=[O:8])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[CH3:10][O:11][C:12]1[CH:18]=[CH:17][C:16]([O:19][CH3:20])=[CH:15][C:13]=1[NH2:14].C(OCC)(=O)C.CCCCCCC>O>[CH3:10][O:11][C:12]1[CH:18]=[CH:17][C:16]([O:19][CH3:20])=[CH:15][C:13]=1[NH:14][C:7]([CH:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1)=[O:8]

Participants

5

Reactant 3

HCID 76132,5-DimethoxyanilineHCID 75938Cyclohexanecarbonyl chlorideHCID 21899848Ethylacetate heptane

Product 1

HCID 531821N-(2,5-dimethoxyphenyl)cyclohexanecarboxamideYield 80.5%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
70 °C

Procedure

1 ml (7.62 mmol, 1.1 eq.) of cyclohexanoic acid chloride is added to a solution of 1.05 g (6.89 mmol) of 2,5-dimethoxyaniline in 10 ml of a mixture toluene/methanol (1/1). The reaction mixture is maintained under stirring at 70° C. for 1.5 hour, and, after returning to ambient temperature, is poured into 50 ml of water. The expected product is extracted twice with 50 ml of toluene, then washed twice with 50 ml of water. The organic phases are combined, dried over magnesium sulphate and the solvent evaporated off under reduced pressure. 1.46 g (yield=67%) of N-(2,5-dimethoxyphenyl)cyclohexanecarboxamide is obtained and used without other purification in the following stage.

Workup

  1. temperatureThe reaction mixture is maintained
  2. customafter returning to ambient temperature
  3. extractionThe expected product is extracted twice with 50 ml of toluene
  4. washwashed twice with 50 ml of water
  5. dry with materialdried over magnesium sulphate
  6. customthe solvent evaporated off under reduced pressure

Sources & evidence

ORD record
ord-e67b8ed6d7574bf481cc35b94c6e4a36
Source dataset
uspto-grants-2007_10
Patent number
US07279467B2

Reaction notes

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