Phenethyl Isothiocyanate → 1-(1H-indol-5-ylmethyl)-3-phenethylthiourea

HRID 656259

Reaction equation

HRID 656259 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][C:6]([CH2:10][NH2:11])=[CH:7][CH:8]=2)[CH:3]=[CH:2]1.[CH2:12]([N:20]=[C:21]=[S:22])[CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1>CN(C)C=O.ClCCl>[NH:1]1[C:9]2[C:4](=[CH:5][C:6]([CH2:10][NH:11][C:21]([NH:20][CH2:12][CH2:13][C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)=[S:22])=[CH:7][CH:8]=2)[CH:3]=[CH:2]1

Participants

5

Reactant 2

HCID 16741Phenethyl IsothiocyanateHCID 54791(1H-indol-5-yl)methanamine

Product 1

HCID 590880511-(1H-indol-5-ylmethyl)-3-phenethylthioureaYield 83%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Procedure

(1H-indol-5-yl)methylamine (8.5 mg) prepared in Step 1 was dissolved in dimethylformamide (100 μl) and the solution was diluted with dichloromethane (1 ml). To the diluted solution was added phenethylisothiocyanate (40 μl) and the mixture was stirred at room temperature for 2 hours. The resulting mixture was concentrated under reduced pressure and the obtained residue was chromatographed on a silica gel column eluting with ethyl acetate/hexane (2/3) to yield 1-(1H-indol-5-ylmethyl)-3-phenethylthiourea (15 mg, 83%).

Workup

  1. concentrationThe resulting mixture was concentrated under reduced pressure
  2. customthe obtained residue was chromatographed on a silica gel column
  3. washeluting with ethyl acetate/hexane (2/3)

Sources & evidence

ORD record
ord-f2de0c308d394d2782bb9941f6562262
Source dataset
uspto-grants-2011_12
Patent number
US08071650B2

Linked notes

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