Toluene → N-Cyclohexyl-N-methylethanimidamide

HRID 596666Notes

Reaction equation

HRID 596666 reaction equation
C[N:2]=[C:3](OC)[CH3:4].[CH:7]1([NH2:13])[CH2:12][CH2:11][CH2:10][CH2:9][CH2:8]1.[C:14]1(C)C=CC=CC=1>>[CH:7]1([N:13]([CH3:14])[C:3](=[NH:2])[CH3:4])[CH2:12][CH2:11][CH2:10][CH2:9][CH2:8]1

Participants

4

Reactant 3

HCID 1140TolueneHCID 7965CyclohexylamineHCID 5207803619-34-9

Product 1

HCID 53432262N-Cyclohexyl-N-methylethanimidamide

Procedure

To a solution of methyl N-methylacetimidate (8.7 g, 0.1m) in toluene (90 ml.) was added cyclohexylamine (10.5 g, 0.105m). After 72 hours at room temperature and 32 hours heating at 60°-70° C the solvent was removed by evaporation to yield an oil which crystallised on cooling. Chromatography on alumina using ether as eluent afforded N-cyclohexyl-N1 -methylacetamidine as a colourless solid (11 g), or m.p. 108.5° - 109.5° C.

Workup

  1. temperature32 hours heating at 60°-70° C the solvent
  2. customwas removed by evaporation
  3. customto yield an oil which
  4. customcrystallised
  5. temperatureon cooling

Sources & evidence

ORD record
ord-9167b5cebac842b294809db192905082
Source dataset
uspto-grants-1977_03
Patent number
US04011343

Reaction notes

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