Methyl Isocyanate → N-[2-[[[5-(dimethylamino)methyl-2-furanyl]methyl]thio]ethyl]-N'-methylurea

HRID 65750

Reaction equation

HRID 65750 reaction equation
[CH3:1][N:2]=[C:3]=[O:4].[CH3:5][N:6]([CH2:8][C:9]1[O:13][C:12]([CH2:14][S:15][CH2:16][CH2:17][NH2:18])=[CH:11][CH:10]=1)[CH3:7]>C(#N)C>[CH3:7][N:6]([CH2:8][C:9]1[O:13][C:12]([CH2:14][S:15][CH2:16][CH2:17][NH:18][C:3]([NH:2][CH3:1])=[O:4])=[CH:11][CH:10]=1)[CH3:5]

Participants

4

Reactant 2

HCID 12228Methyl IsocyanateHCID 1622035-(((2-Aminoethyl)thio)methyl)-N,N-dimethyl-2-furanmethanamine

Product 1

HCID 13432083N-[2-[[[5-(dimethylamino)methyl-2-furanyl]methyl]thio]ethyl]-N'-methylurea

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Methylisocyanate (0.33 g) was added to a suspension of 2-[[[5-(dimethylamino)methyl-2-furanyl]methyl]thio]ethanamine, phthalhydrazide complex (2 g) in acetonitrile (50 ml). After 2 hr the solution was filtered and the filtrate evaporated to give an oil which was purified by column chromatography (silica/methanol) to give N-[2-[[[5-(dimethylamino)methyl-2-furanyl]methyl]thio]ethyl]-N'-methylurea. Analysis Found: C, 52.38; H, 7.61; N, 15.25. C12H21N3O2S.1/4H2O requires: C, 52.24; H, 7.76; N, 15.32%.

Workup

  1. filtrationAfter 2 hr the solution was filtered
  2. customthe filtrate evaporated
  3. customto give an oil which
  4. customwas purified by column chromatography (silica/methanol)

Sources & evidence

ORD record
ord-bd0f53620b164f1095718dad59841bc4
Source dataset
uspto-grants-1978_12
Patent number
US04128658

Linked notes

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