Methyl isothiocyanate → N-Methyl-N'-(2-{[(pyridin-4-yl)methyl]amino}ethyl)thiourea

HRID 1580074Notes

Reaction equation

HRID 1580074 reaction equation
[CH3:1][N:2]=[C:3]=[S:4].[N:5]1[CH:10]=[CH:9][C:8]([CH2:11][NH:12][CH2:13][CH2:14][NH2:15])=[CH:7][CH:6]=1>C(O)C>[CH3:1][NH:2][C:3]([NH:15][CH2:14][CH2:13][NH:12][CH2:11][C:8]1[CH:7]=[CH:6][N:5]=[CH:10][CH:9]=1)=[S:4]

Participants

4

Reactant 2

HCID 11167Methyl isothiocyanateHCID 81575N-(4-Pyridylmethyl)ethylenediamine

Product 1

HCID 21441086N-Methyl-N'-(2-{[(pyridin-4-yl)methyl]amino}ethyl)thiourea

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Methylisothiocyanate (1.46 g.) was added slowly to a solution of N-(4-picolyl)ethylenediamine (3.3 g.) in ethanol (25 ml.) The mixture was heated under reflux for 0.5 hours concentrated and extracted with isopropyl acetate to remove N-4-picolyl-N,N'-dimethylethane-1,2-bis thiourea (m.p. 173°-174°). The mother liquors were concentrated and the residue purified by column chromatography to afford the title compound.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 0.5 hours
  3. concentrationconcentrated
  4. extractionextracted with isopropyl acetate
  5. customto remove N-4-picolyl-N,N'-dimethylethane-1,2-bis thiourea (m.p. 173°-174°)
  6. concentrationThe mother liquors were concentrated
  7. customthe residue purified by column chromatography

Sources & evidence

ORD record
ord-a6e187a53e3e490ab0ba0e0eb2d1ee84
Source dataset
uspto-grants-1976_01
Patent number
US03932427

Reaction notes

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