Methyl isothiocyanate → N-Methyl-N'-[2-[[3-(N,N-dimethylaminomethyl)phenyl]methylthio]ethyl]thiourea

HRID 1493184Notes

Reaction equation

HRID 1493184 reaction equation
[CH3:1][N:2]([CH2:4][C:5]1[CH:6]=[C:7]([CH2:11][S:12][CH2:13][CH2:14][NH2:15])[CH:8]=[CH:9][CH:10]=1)[CH3:3].[CH3:16][N:17]=[C:18]=[S:19]>C(#N)C>[CH3:16][NH:17][C:18]([NH:15][CH2:14][CH2:13][S:12][CH2:11][C:7]1[CH:8]=[CH:9][CH:10]=[C:5]([CH2:4][N:2]([CH3:1])[CH3:3])[CH:6]=1)=[S:19]

Participants

4

Reactant 2

HCID 11167Methyl isothiocyanateHCID 129520192-[[3-(N,N-Dimethylaminomethyl)phenyl]methylthio]ethanamine

Product 1

HCID 86744815N-Methyl-N'-[2-[[3-(N,N-dimethylaminomethyl)phenyl]methylthio]ethyl]thiourea

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

2-[[3-(N,N-Dimethylaminomethyl)phenyl]methylthio]ethanamine (5 g) and methyl isothiocyanate (1.62 g) were stirred at room temperature in acetonitrile for 18 hours. The solvent was removed and the residue was column chromatographed on silica using a mixture of ethyl acetate and methanol as eluent to give the title compound as a pale yellow oil. TLC silica; ethyl acetate:isopropanol:water:0.88 ammonia (25:15:8:2) Rf 0.61.

Workup

  1. customThe solvent was removed
  2. customchromatographed on silica using
  3. additiona mixture of ethyl acetate and methanol as eluent

Sources & evidence

ORD record
ord-04f5ef278ce147c68455c782963f3a1d
Source dataset
uspto-grants-1991_06
Patent number
US05021429

Reaction notes

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