Cyclohexylamine → N-Cyclohexylacetoacetamide

HRID 1730616

Reaction equation

HRID 1730616 reaction equation
[CH2:1]=[C:2]1[O:6][C:4](=[O:5])[CH2:3]1.[CH:7]1([NH2:13])[CH2:12][CH2:11][CH2:10][CH2:9][CH2:8]1>C1C=CC=CC=1>[CH:7]1([NH:13][C:4](=[O:5])[CH2:3][C:2]([CH3:1])=[O:6])[CH2:12][CH2:11][CH2:10][CH2:9][CH2:8]1

Participants

4

Reactant 2

HCID 7965CyclohexylamineHCID 12661Diketene

Product 1

HCID 70805N-Cyclohexylacetoacetamide

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent2×

Procedure

A solution of diketene (42 g.) in benzene (74 ml.) is added dropwise with vigorous stirring to a solution of cyclohexylamine (49.6 g.) in benzene (125 ml.). The rate of addition is adjusted so that a gentle reflux is maintained. The benzene is removed under vacuum and the yellow oil crystallizes upon trituation with hexane. A yield of 88.7 g. of product melting at 66°-69° C. is obtained.

Workup

  1. additionThe rate of addition
  2. temperaturea gentle reflux
  3. temperatureis maintained
  4. customThe benzene is removed under vacuum
  5. customthe yellow oil crystallizes upon trituation with hexane

Sources & evidence

ORD record
ord-f41e8808f013472d95e642b7057a0f3c
Source dataset
uspto-grants-1976_11
Patent number
US03993637

Linked notes

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