Ammonia → Acrylamide, N-cyclohexyl-

HRID 1732232Notes

Reaction equation

HRID 1732232 reaction equation
CO[CH2:3][CH2:4][C:5]([NH2:7])=[O:6].[CH:8]1(N)[CH2:13][CH2:12][CH2:11][CH2:10][CH2:9]1.N.[OH-].[Na+]>>[CH:8]1([NH:7][C:5](=[O:6])[CH:4]=[CH2:3])[CH2:13][CH2:12][CH2:11][CH2:10][CH2:9]1

Participants

5

Reactant 4

HCID 222AmmoniaHCID 7965CyclohexylamineHCID 14798Sodium HydroxideHCID 52524813-Methoxypropanamide

Product 1

HCID 137811Acrylamide, N-cyclohexyl-

Procedure

103.1 g (1.0 mole) of 3-methoxypropionamide are heated with 104.1 g (1.05 mole) of cyclohexylamine for 8 hours in a temperature range of 130°-170° C. until the evolution of ammonia is complete. The mixture is allowed to cool, 1.5 g of sodium hydroxide is added and the mixture is heated in a high vacuum at 90°-110° C. The methanol is split off within about 30 minutes, vigorous foaming occurring. The temperature is increased and 93.5 g (0.61 mole=61% of the theoretical yield) of N-cyclohexylacrylamide having a Bp0.1 of 124°-128° C., which solidifies into crystalline form in the receiver, are distilled off.

Workup

  1. temperatureto cool
  2. temperaturethe mixture is heated in a high vacuum at 90°-110° C
  3. customThe methanol is split off within about 30 minutes
  4. temperatureThe temperature is increased

Sources & evidence

ORD record
ord-bd65b2df867f48398120a128bcecd266
Source dataset
uspto-grants-1980_12
Patent number
US04237067

Reaction notes

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