Benzoyl chloride → N-Cyclohexylbenzamide

HRID 223248Notes

Reaction equation

HRID 223248 reaction equation
[CH:1]1([NH2:7])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[C:8](Cl)(=[O:15])[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1>C1C=CC=CC=1>[CH:1]1([NH:7][C:8](=[O:15])[C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

4

Reactant 2

HCID 7412Benzoyl chlorideHCID 7965Cyclohexylamine

Product 1

HCID 15657N-CyclohexylbenzamideYield 84%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

18 g of cyclohexylamine was dissolved in 150 ml of benzene. To the resulting solution was very slowly added 20 g of benzoyl chloride with stirring at temperatures below 40° C. White crystals separated from the mixture, generating white smoke. The mixture was stirred for one hour and was then made alkaline by addition of pyridine thereto. The product was filtered with suction. Crude crystals melting at 142° C. to 144° C. were recrystallized from a mixture of methanol and ethanol (1:1 in volume), from which white needles melting at 144° C. to 145° C. separated. The yield was 84%.

Workup

  1. customWhite crystals separated from the mixture
  2. stirringThe mixture was stirred for one hour
  3. additionby addition of pyridine
  4. filtrationThe product was filtered with suction
  5. customCrude crystals melting at 142° C. to 144° C. were recrystallized from a mixture of methanol and ethanol (1:1 in volume), from which white needles melting at 144° C. to 145° C.
  6. customseparated

Sources & evidence

ORD record
ord-0043fec0294648f3abdcc46f20d63d7f
Source dataset
uspto-grants-1982_10
Patent number
US04352860

Reaction notes

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