Sulfuric Acid → 1-Aminocyclohexanecarboxamide

HRID 328365Notes

Reaction equation

HRID 328365 reaction equation
S(=O)(=O)(O)O.[NH2:6][C:7]1([C:13]#[N:14])[CH2:12][CH2:11][CH2:10][CH2:9][CH2:8]1.[OH-:15].[Na+]>>[NH2:6][C:7]1([C:13]([NH2:14])=[O:15])[CH2:12][CH2:11][CH2:10][CH2:9][CH2:8]1

Participants

4

Reactant 3

HCID 1118Sulfuric AcidHCID 14798Sodium HydroxideHCID 796351-Aminocyclohexanecarbonitrile

Product 1

HCID 112405481-Aminocyclohexanecarboxamide

Conditions

Temperature
100 °C

Procedure

To 20 g concentrated sulfuric acid at 5° C is added with stirring 10 g of 1-aminocyclohexanecarbonitrile. After the addition, the mixture is heated with stirring at 100° C for 1 hour. The hot solution is then poured onto ice, the solution made strongly basic with 50% aqueous sodium hydroxide solution, and extracted three times with chloroform. The extract is washed with water, saturated NaHCO3 solution, dried, and the solvent removed in vacuo to leave the product, 1-aminocyclohexanecarboxamide, as a crystalline residue, melting point 99°-102° C. This can be recrystallized from either benzene or ether to give a pure product, melting point 101°-102° C.

Workup

  1. additionAfter the addition
  2. temperaturethe mixture is heated
  3. additionThe hot solution is then poured onto ice
  4. extractionextracted three times with chloroform
  5. washThe extract is washed with water, saturated NaHCO3 solution
  6. customdried
  7. customthe solvent removed in vacuo

Sources & evidence

ORD record
ord-3f0beffc39e1416b9e605d744d30c323
Source dataset
uspto-grants-1977_04
Patent number
US04017510

Reaction notes

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