Methyl isothiocyanate → N-methyl-N'-methyl-N'-3-pyridylmethylthiourea

HRID 249506Notes

Reaction equation

HRID 249506 reaction equation
[CH3:1][NH:2][CH2:3][C:4]1[CH:5]=[N:6][CH:7]=[CH:8][CH:9]=1.[CH3:10][N:11]=[C:12]=[S:13]>C1(C)C=CC=CC=1>[CH3:10][NH:11][C:12]([N:2]([CH3:1])[CH2:3][C:4]1[CH:5]=[N:6][CH:7]=[CH:8][CH:9]=1)=[S:13]

Participants

4

Reactant 2

HCID 11167Methyl isothiocyanateHCID 883933-(Methylaminomethyl)pyridine

Product 1

HCID 22450305N-methyl-N'-methyl-N'-3-pyridylmethylthioureaYield 97.3%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

In 30 ml of toluene was dissolved 2.5 g (0.02 mole) of N-methyl-N-3-pyridylmethylamine followed by addition of 1.5 g (0.02 mole) of methyl isothiocyanate and the mixture was stirred at room temperature overnight. Finally, the solvent was distilled off to give 3.8 g of N-methyl-N'-methyl-N'-3-pyridylmethylthiourea as a yellow viscous oil. This oily product was purified by silica gel column chromatography using HeOH-CHCl3 (1:10) as an eluent to give crystals.

Workup

  1. distillationFinally, the solvent was distilled off

Sources & evidence

ORD record
ord-ca61bb5a06cf462f9d46e38da0dc8d65
Source dataset
uspto-grants-1993_05
Patent number
US05214152

Reaction notes

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