Cyclohexylamine → N-Cyclohexyl-2-methylbenzene-1-carboximidic acid

HRID 918185Notes

Reaction equation

HRID 918185 reaction equation
[CH:1]1([NH2:7])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[CH3:8][C:9]1[CH:17]=[CH:16][CH:15]=[CH:14][C:10]=1[C:11](Cl)=[O:12].C(N(CC)CC)C>C1C=CC=CC=1>[CH:1]1([NH:7][C:11](=[O:12])[C:10]2[CH:14]=[CH:15][CH:16]=[CH:17][C:9]=2[CH3:8])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

5

Reactant 3

HCID 7965CyclohexylamineHCID 8471TriethylamineHCID 702762-Methylbenzoyl chloride

Product 1

HCID 226940N-Cyclohexyl-2-methylbenzene-1-carboximidic acid

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Conditions

Temperature
60 °C

Procedure

9.9 PARTS OF CYCLOHEXYLAMINE IS DISSOLVED IN 100 PARTS OF BENZENE AND THE MIXTURE IS REACTED WITH 15.5 PARTS OF 2-METHYLBENZOYL CHLORIDE IN THE PRESENCE OF 12 PARTS OF TRIETHYLAMINE AT 10°C. The whole is stirred for 3 hours at 60°C and then cooled; the precipitated triethylamine chloride is filtered, the filtrate is concentrated under vacuum and the residue is recrystallized from a mixture of methanol and water.

Workup

  1. temperaturecooled
  2. filtrationthe precipitated triethylamine chloride is filtered
  3. concentrationthe filtrate is concentrated under vacuum
  4. customthe residue is recrystallized from a mixture of methanol and water

Sources & evidence

ORD record
ord-fc31fa5d9a444c4794ed8fb016a96e9f
Source dataset
uspto-grants-1976_07
Patent number
US03969510

Reaction notes

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