O-Toluidine → 1-Methyl-N-(2-methylphenyl)cyclohexane-1-carboxamide

HRID 1288042Notes

Reaction equation

HRID 1288042 reaction equation
[CH3:1][C:2]1([C:8](Cl)=[O:9])[CH2:7][CH2:6][CH2:5][CH2:4][CH2:3]1.C(=O)([O-])[O-].[K+].[K+].[NH2:17][C:18]1[C:19]([CH3:24])=[CH:20][CH:21]=[CH:22][CH:23]=1>C1(C)C=CC=CC=1>[CH3:1][C:2]1([C:8]([NH:17][C:18]2[C:19]([CH3:24])=[CH:20][CH:21]=[CH:22][CH:23]=2)=[O:9])[CH2:7][CH2:6][CH2:5][CH2:4][CH2:3]1

Participants

5

Reactant 3

HCID 7242O-ToluidineHCID 11430Potassium CarbonateHCID 41892451-Methylcyclohexanecarbonyl chloride

Product 1

HCID 127516481-Methyl-N-(2-methylphenyl)cyclohexane-1-carboxamide

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A mixture of 32.7 grams (0.203 moles) of 1-methyl-1-cyclohexanecarboxylic acid chloride, 15.2 grams (0.11 mole) of anhydrous potassium carbonate and 21.8 grams (0.203 mole) of o-toluidine in 260 ml. of dry toluene is stirred and refluxed for 2.5 hours. The inorganic salts are removed by filtration and the filtrate is concentrated in vacuuo. The residue yields from diethyl ether-pentane 40.5 grams (87%) of N-(1-methylcyclohexyl carbonyl)-o-toluidine; m.p. 138° C.

Workup

  1. temperaturerefluxed for 2.5 hours
  2. customThe inorganic salts are removed by filtration
  3. concentrationthe filtrate is concentrated in vacuuo

Sources & evidence

ORD record
ord-e549e00b74e4479fa38b5559650dafbe
Source dataset
uspto-grants-1976_10
Patent number
US03987059

Reaction notes

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