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

HRID 845755Notes

Reaction equation

HRID 845755 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-11e052adab59470f83e40e268421b037
Source dataset
uspto-grants-1988_07
Patent number
US04760075

Reaction notes

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