Ethyl Acetate → HCID 53698835, compound

HRID 861606Notes

Reaction equation

HRID 861606 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:21]=[C:22](CCN)[CH:23]=[CH:24][CH:25]=1.C(OCC)(=O)C>CN(C)C=O>[CH3:18][O:19][C:20]1[CH:25]=[C:24]([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:23]=[CH:22][CH:21]=1

Participants

5

Reactant 3

HCID 8857Ethyl AcetateHCID 748663-MethoxyphenethylamineHCID 19704123N-(1H-benzo[d]imidazol-2-yl)-1H-imidazole-1-carbothioamide

Product 1

HCID 53698835HCID 53698835, compoundYield 73.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 1-[(2-benzimidazolyl)thiocarbamoyl]imidazole (1.22 g, 5.0 mmol) and 2-(3-methoxyphenyl)ethylamine (0.78 g, 5.0 mmol) in N,N-dimethylformamide (20 mL) was stirred at 90° C. for 2 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 1.2 g (73%) 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-ee2b5fac8a4c45f58678afb76e2825f2
Source dataset
uspto-grants-1998_02
Patent number
US05714503

Reaction notes

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