Hydrochloric Acid → N-octadecylbenzamide

HRID 223249Notes

Reaction equation

HRID 223249 reaction equation
[CH2:1]([NH2:19])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH3:18].[C:20](Cl)(=[O:27])[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1.Cl>C1(C)C=CC=CC=1>[CH2:1]([NH:19][C:20](=[O:27])[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH3:18]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 7412Benzoyl chlorideHCID 15793Octadecylamine

Product 1

HCID 4570775N-octadecylbenzamideYield 83%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
80 °C

Procedure

27 g of stearylamine was dispersed in 100 ml of toluene. To this dispersion was added 13 g of benzoyl chloride at 70° C. An exothermic reaction occurred and the temperature of the mixture increased to 80° C. The reaction mixture was heated to 100° C. and that temperature was maintained for about 20 hours until generation of hydrogen chloride gas was terminated. The reaction mixture was cooled, from which white crude crystals were separated. The thus obtained white crystals were neutralized with sodium hydroxide and were then recrystallized from alcohol. This recrystallization gave white crystals melting at 85° C. to 87° C. The yield was 83%.

Workup

  1. customAn exothermic reaction
  2. temperatureThe reaction mixture was heated to 100° C.
  3. customwas terminated
  4. temperatureThe reaction mixture was cooled, from which white crude crystals
  5. customwere separated
  6. customwere then recrystallized from alcohol
  7. customThis recrystallization

Sources & evidence

ORD record
ord-eea535bc31c349f795e17d7b2046e2db
Source dataset
uspto-grants-1982_10
Patent number
US04352860

Reaction notes

Loading…