Allyl Isothiocyanate → N-[2-(6-dimethylaminomethyl-2-benzofuranylmethylthio)ethyl]-N'-(2-propenyl)thiourea

HRID 1732582Notes

Reaction equation

HRID 1732582 reaction equation
[NH2:1][CH2:2][CH2:3][S:4][CH2:5][C:6]1[O:7][C:8]2[CH:14]=[C:13]([CH2:15][N:16]([CH3:18])[CH3:17])[CH:12]=[CH:11][C:9]=2[CH:10]=1.[CH2:19]([N:22]=[C:23]=[S:24])[CH:20]=[CH2:21]>C(#N)C>[CH3:17][N:16]([CH2:15][C:13]1[CH:12]=[CH:11][C:9]2[CH:10]=[C:6]([CH2:5][S:4][CH2:3][CH2:2][NH:1][C:23]([NH:22][CH2:19][CH:20]=[CH2:21])=[S:24])[O:7][C:8]=2[CH:14]=1)[CH3:18]

Participants

4

Reactant 2

HCID 5971Allyl IsothiocyanateHCID 203039642-(2-Aminoethylthiomethyl)-6-(dimethylaminomethyl)benzofuran

Product 1

HCID 20303954N-[2-(6-dimethylaminomethyl-2-benzofuranylmethylthio)ethyl]-N'-(2-propenyl)thiourea

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A solution of 2-(2-aminoethylthiomethyl)-6-(dimethylaminomethyl)benzofuran (Example 1, Step E) (2.6 g., 0.01 mole) and allyl isothiocyanate (1.1 g., 0.011 mole) in acetonitrile (15 ml.) is kept at 25°-27° C. for 16 hours. The solvent is evaporated and the residual oil chromatographed (silica gel/5% methanol in chloroform) to yield N-[2-(6-dimethylaminomethyl-2-benzofuranylmethylthio)ethyl]-N'-(2-propenyl)thiourea.

Workup

  1. customThe solvent is evaporated
  2. customthe residual oil chromatographed (silica gel/5% methanol in chloroform)

Sources & evidence

ORD record
ord-83a720232473431aa1fbe6110f92cfbf
Source dataset
uspto-grants-1980_12
Patent number
US04238487

Reaction notes

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