2-Methoxyethyl isothiocyanate → N-[2-[[[5-(dimethylamino)methyl-2-furanyl]methyl]thio]ethyl]-N'-(2-methoxyethyl)thiourea

HRID 1277875Notes

Reaction equation

HRID 1277875 reaction equation
[N:1]([CH2:4][CH2:5][O:6][CH3:7])=[C:2]=[S:3].[CH3:8][N:9]([CH2:11][C:12]1[O:16][C:15]([CH2:17][S:18][CH2:19][CH2:20][NH2:21])=[CH:14][CH:13]=1)[CH3:10]>C(#N)C>[CH3:10][N:9]([CH2:11][C:12]1[O:16][C:15]([CH2:17][S:18][CH2:19][CH2:20][NH:21][C:2]([NH:1][CH2:4][CH2:5][O:6][CH3:7])=[S:3])=[CH:14][CH:13]=1)[CH3:8]

Participants

4

Reactant 2

HCID 1234752-Methoxyethyl isothiocyanateHCID 1622035-(((2-Aminoethyl)thio)methyl)-N,N-dimethyl-2-furanmethanamine

Product 1

HCID 23452142N-[2-[[[5-(dimethylamino)methyl-2-furanyl]methyl]thio]ethyl]-N'-(2-methoxyethyl)thiourea

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

1-(Isothiocyanato)-2-methoxyethane (1.17 g) and 2-[[[5-(dimethylamino)methyl-2-furanyl]methyl]thio]ethanamine (2.14 g) in acetonitrile were stood overnight. Solvent was removed and the residual oil chromatographed (silica/methanol) to give N-[2-[[[5-(dimethylamino)methyl-2-furanyl]methyl]thio]ethyl]-N'-(2-methoxyethyl)thiourea as a pale oil Rf 0.45. Analysis Found: C, 50.64; H, 7.51; N, 12.58. C14H25N3O2S2 requires: C, 50.75; H, 7.55; N, 12.69%.

Workup

  1. customSolvent was removed
  2. customthe residual oil chromatographed (silica/methanol)

Sources & evidence

ORD record
ord-9d24a1b46bff40ef8b4e6770323554c5
Source dataset
uspto-grants-1981_07
Patent number
US04279819

Reaction notes

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