O-Methyltyramine → HCID 53896895, compound

HRID 2257792Notes

Reaction equation

HRID 2257792 reaction equation
[N:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[NH:3][C:2]=1[NH:10][C:11]([N:13]1[CH:17]=[CH:16]N=C1)=[S:12].[CH3:18][O:19][C:20]1[CH:25]=[CH:24][C:23](CCN)=[CH:22][CH:21]=1.C(OCC)(=O)C>CN(C)C=O>[CH3:18][O:19][C:20]1[CH:25]=[CH:24][C:23]([CH2:16][CH2:17][NH:13][C:11]([NH:10][C:2]2[NH:1][C:5]3[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=3[N:3]=2)=[S:12])=[CH:22][CH:21]=1

Participants

5

Reactant 3

HCID 4657O-MethyltyramineHCID 8857Ethyl AcetateHCID 19704123N-(1H-benzo[d]imidazol-2-yl)-1H-imidazole-1-carbothioamide

Product 1

HCID 53896895HCID 53896895, compoundYield 67.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 1-[(2-benzimidazolyl)thiocarbamoyl]imidazole (1.22 g, 5.0 mmol) and 2-(4-methoxyphenyl)ethylamine (0.77 g, 5.0 mmol) in N,N-dimethylformamide (20 mL) was stirred at 90° C. for 1 h. The reaction was cooled to room temperature, poured into ethyl acetate, washed with water, 1N aqueous HCl, water, saturated sodium bicarbonate, and brine. The organic layer was concentrated and the resultant solid was purified by chromatography on silica gel to provide 1.1 g (67%) of the titled product as a white solid:

Workup

  1. washwashed with water, 1N aqueous HCl, water, saturated sodium bicarbonate, and brine
  2. concentrationThe organic layer was concentrated
  3. customthe resultant solid was purified by chromatography on silica gel

Sources & evidence

ORD record
ord-94d9ffb6caac4b8fb1dfb65c39f416de
Source dataset
uspto-grants-1997_08
Patent number
US05658907

Reaction notes

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