Methyl isothiocyanate → N-methyl-N'-2-(2-dimethylaminomethyl-4-thiazolylmethylthio)ethylthiourea

HRID 1200242Notes

Reaction equation

HRID 1200242 reaction equation
[CH3:1][N:2]([CH2:4][C:5]1[S:6][CH:7]=[C:8]([CH2:10][S:11][CH2:12][CH2:13][NH2:14])[N:9]=1)[CH3:3].[CH3:15][N:16]=[C:17]=[S:18]>C(O)C>[CH3:15][NH:16][C:17]([NH:14][CH2:13][CH2:12][S:11][CH2:10][C:8]1[N:9]=[C:5]([CH2:4][N:2]([CH3:1])[CH3:3])[S:6][CH:7]=1)=[S:18]

Participants

4

Reactant 2

HCID 11167Methyl isothiocyanateHCID 109773182-(Dimethylaminomethyl)-4-(2-aminoethylthiomethyl)thiazole

Product 1

HCID 15053483N-methyl-N'-2-(2-dimethylaminomethyl-4-thiazolylmethylthio)ethylthiourea

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution was prepared containing 0.80 g. of 2-(2-dimethylaminomethyl-4-thiazolylmethylthio)ethylamine and 0.29 g. of methylisothiocyanate in 10 ml. of ethanol. The solution was stirred at room temperature for about 17 hours after which time the solvent was removed by evaporation in vacuo. The residual gum, comprising N-methyl-N'-2-(2-dimethylaminomethyl-4-thiazolylmethylthio)ethylthiourea formed in the above reaction, was purified by chromatography over silica using a gradient elution technique with ethyl acetate containing increasing quantities of methanol as the eluant. Fractions containing the above compound were combined and the solvent evaporated therefrom in vacuo, leaving as a residue 0.83 g. of a glassy solid.

Workup

  1. customA solution was prepared
  2. additioncontaining 0.80 g
  3. customwas removed by evaporation in vacuo
  4. customformed in the above reaction
  5. customwas purified by chromatography over silica using
  6. washa gradient elution technique with ethyl acetate containing
  7. temperatureincreasing quantities of methanol as the eluant
  8. additionFractions containing the above compound
  9. customthe solvent evaporated
  10. customin vacuo, leaving as a residue 0.83 g

Sources & evidence

ORD record
ord-34d110e9d3534ea6b6ed3770dc649bd4
Source dataset
uspto-grants-1990_02
Patent number
US04904792

Reaction notes

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