Furfurylamine → 1-(Furan-2-ylmethyl)-3-(4-methoxybenzyl)thiourea

HRID 656283Notes

Reaction equation

HRID 656283 reaction equation
[O:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[CH2:6][NH2:7].C(N(CC)CC)C.[CH3:15][O:16][C:17]1[CH:26]=[CH:25][C:20]([CH2:21][N:22]=[C:23]=[S:24])=[CH:19][CH:18]=1>CN(C)C=O.C(OCC)(=O)C>[O:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[CH2:6][NH:7][C:23]([NH:22][CH2:21][C:20]1[CH:25]=[CH:26][C:17]([O:16][CH3:15])=[CH:18][CH:19]=1)=[S:24]

Participants

6

Reactant 3

HCID 3438FurfurylamineHCID 8471TriethylamineHCID 123197Benzene, 1-(isothiocyanatomethyl)-4-methoxy-

Product 1

HCID 9781801-(Furan-2-ylmethyl)-3-(4-methoxybenzyl)thioureaYield 92.5%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

Furan-2-ylmethylamine (190 mg) was dissolved in dimethylformamide (5 ml) and to the solution were added triethylamine (200 mg) and 4-methoxybenzylisothiocyanate (360 mg), followed by stirring at room temperature for 24 hours. Then, the resulting mixture was diluted with ethyl acetate, washed with water, dried, and concentrated under reduced pressure. The residue was purified by column-chromatography (hexane/ethyl acetate=1/1) to yield the compound 16-1 (0.5 g, 90%) as a liquid.

Workup

  1. washwashed with water
  2. customdried
  3. concentrationconcentrated under reduced pressure
  4. customThe residue was purified by column-chromatography (hexane/ethyl acetate=1/1)

Sources & evidence

ORD record
ord-4aed6ed970074ad2abed7d319ea0de3c
Source dataset
uspto-grants-2011_12
Patent number
US08071650B2

Reaction notes

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