Cyclohexylamine → N-Cyclohexylformamide

HRID 1390855Notes

Reaction equation

HRID 1390855 reaction equation
C1(N)CCCCC1.[CH:8]([NH:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)=[O:9].[Na]>CO>[CH:11]1([NH:10][CH:8]=[O:9])[CH2:16][CH2:15][CH2:14][CH2:13][CH2:12]1

Participants

4

Reactant 2

HCID 7965CyclohexylamineHCID 86736350HCID 86736350, compound

Product 1

HCID 13017N-CyclohexylformamideYield 79%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
100 °C

Procedure

To the reactor described in Example 1, there is placed 99 grams cyclohexylamine, 14 grams (0.1 mole) of sodium formanilide and 150 grams of methanol. The autoclave is closed and purged with carbon monoxide, the temperature raised to 100° C. with atmospheric steam and carbon monoxide introduced at 28 kg/cm2 for about an hour. The reaction mixture is then cooled and vented, 10 milliliters of concentrated hydrochloric acid is added and the solvent is removed by distillation. Benzene is then added and the benzene solution filtered through a bed of filter acid. Distillation gives N-cyclohexyl formamide, boiling point 118°-130° C. at 3 milliliters. The expected yield is about 79%.

Workup

  1. customThe autoclave is closed
  2. custompurged with carbon monoxide
  3. additionintroduced at 28 kg/cm2 for about an hour
  4. temperatureThe reaction mixture is then cooled
  5. addition10 milliliters of concentrated hydrochloric acid is added
  6. customthe solvent is removed by distillation
  7. additionBenzene is then added
  8. filtrationthe benzene solution filtered through a bed of filter acid
  9. distillationDistillation

Sources & evidence

ORD record
ord-ad16ba4aa8de45f3a7652e40cab656b7
Source dataset
uspto-grants-1979_02
Patent number
US04140716

Reaction notes

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