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

HRID 1391212Notes

Reaction equation

HRID 1391212 reaction equation
[CH2:1]([CH:3]1[C:8]2[N:9]=[CH:10][NH:11][C:7]=2[CH2:6][CH2:5][NH:4]1)[CH3:2].[CH3:12][N:13]=[C:14]=[S:15]>C(#N)C.C(O)C>[CH2:1]([CH:3]1[C:8]2[N:9]=[CH:10][NH:11][C:7]=2[CH2:6][CH2:5][N:4]1[C:14](=[S:15])[NH:13][CH3:12])[CH3:2]

Participants

5

Reactant 2

HCID 11167Methyl isothiocyanateHCID 233422924-Ethyl-4,5,6,7-tetrahydro-3H-imidazo[4,5-c]pyridine

Product 1

HCID 213307644-ethyl-5-(N-methyl-thiocarbamoyl)-4,5,6,7-tetrahydro-imidazo-[4,5-c]-pyridineYield 69.7%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 6342AcetonitrileSolvent

Procedure

A solution of 2.9 g of 4-ethyl-4,5,6,7-tetrahydro-imidazo-[4,5-c]-pyridine (Farmaco, Ed. Sci. 1967, 22, 821) and 3 g of methyl isothiocyanate in 32 ml of acetonitrile and 8 ml of ethanol is refluxed for 8 h. The solution is evaporated in vacuo, and the residue crystallized from diethyl ether to give 3 g of 4-ethyl-5-(N-methyl-thiocarbamoyl)-4,5,6,7-tetrahydro-imidazo-[4,5-c]-pyridine, m.p. 230°.

Workup

  1. customThe solution is evaporated in vacuo
  2. customthe residue crystallized from diethyl ether

Sources & evidence

ORD record
ord-8eb34597ddbf433797f0271c8a28ac07
Source dataset
uspto-grants-1979_02
Patent number
US04141899

Reaction notes

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