Methyl isothiocyanate → 4-Cyclohexyl-5-(N-methyl-thiocarbamoyl)-4,5,6,7-tetrahydro-imidazo-[4,5-c]-pyridine

HRID 1391224Notes

Reaction equation

HRID 1391224 reaction equation
[CH:1]1([CH:7]2[C:12]3[N:13]=[CH:14][NH:15][C:11]=3[CH2:10][CH2:9][NH:8]2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[CH3:16][N:17]=[C:18]=[S:19]>C(#N)C>[CH:1]1([CH:7]2[C:12]3[N:13]=[CH:14][NH:15][C:11]=3[CH2:10][CH2:9][N:8]2[C:18](=[S:19])[NH:17][CH3:16])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1

Participants

4

Reactant 2

HCID 11167Methyl isothiocyanateHCID 21330712HCID 21330712, compound

Product 1

HCID 213307544-Cyclohexyl-5-(N-methyl-thiocarbamoyl)-4,5,6,7-tetrahydro-imidazo-[4,5-c]-pyridine

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Operating as in Example 14, 15.5 g of 4-cyclohexyl-4,5,6,7-tetrahydro-imidazo-[4,5-c]-pyridine, m.p. 150°, are obtained from 18.4 g of histamine dihydrochloride and 24.4 ml of hexahydrobenzaldehyde. A solution of 2.05 g of 4-cyclohexyl-4,5,6,7-tetrahydro-imidazo-[4,5-c]-pyridine and 1.1 g of methyl isothiocyanate in 30 ml of acetonitrile is refluxed for 5 h. The solution is cooled and filtered, and 2.50 g of the title compound, m.p. 232°, are collected.

Workup

  1. temperatureThe solution is cooled
  2. filtrationfiltered
  3. custom2.50 g of the title compound, m.p. 232°, are collected

Sources & evidence

ORD record
ord-6303064eaa69489c9a2b7d51de825632
Source dataset
uspto-grants-1979_02
Patent number
US04141899

Reaction notes

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