Methyl isothiocyanate → ether N-[5-(5-(dimethylamino)methyl-2-furanyl]pentyl]-N'-methylthiourea

HRID 65747Notes

Reaction equation

HRID 65747 reaction equation
[CH3:1][N:2]([CH2:4][C:5]1[O:9][C:8]([CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][NH2:15])=[CH:7][CH:6]=1)[CH3:3].[CH3:16][N:17]=[C:18]=[S:19]>C(#N)C>[CH3:7][CH2:8][O:9][CH2:5][CH3:4].[CH3:1][N:2]([CH2:4][C:5]1[O:9][C:8]([CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][NH:15][C:18]([NH:17][CH3:16])=[S:19])=[CH:7][CH:6]=1)[CH3:3]

Participants

4

Reactant 2

HCID 11167Methyl isothiocyanateHCID 202132895-[5-(Dimethylamino)methyl-2-furanyl]pentanamine

Product 1

HCID 23452166ether N-[5-(5-(dimethylamino)methyl-2-furanyl]pentyl]-N'-methylthiourea

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

5-[5-(Dimethylamino)methyl-2-furanyl]pentanamine (0.5 g) and methylisothiocyanate (0.25 g) were stirred in acetonitrile at room temperature for 24 hr. Solvent was removed and the product purified by column chromatography (silica/methanol) to give after trituration with ether N-[5-(5-(dimethylamino)methyl-2-furanyl]pentyl]-N'-methylthiourea as off-white crystals m.p. 66°-69°.

Workup

  1. customSolvent was removed
  2. customthe product purified by column chromatography (silica/methanol)

Sources & evidence

ORD record
ord-22ef1b9a3b5e41a6b44a780f86eab5f4
Source dataset
uspto-grants-1978_12
Patent number
US04128658

Reaction notes

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