Ethyl Acetate → HCID 53688815, compound

HRID 861604Notes

Reaction equation

HRID 861604 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].[Cl:18][C:19]1[CH:24]=[CH:23][C:22](CCN)=[CH:21][CH:20]=1.C(OCC)(=O)C>CN(C)C=O>[Cl:18][C:19]1[CH:24]=[CH:23][C:22]([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:21][CH:20]=1

Participants

5

Reactant 3

HCID 8857Ethyl AcetateHCID 674302-(4-Chlorophenyl)ethylamineHCID 19704123N-(1H-benzo[d]imidazol-2-yl)-1H-imidazole-1-carbothioamide

Product 1

HCID 53688815HCID 53688815, compoundYield 79.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 1-[(2-benzimidazolyl)thiocarbamoyl]imidazole (1.22 g, 5.0 mmol) and 2-(4-chlorophenyl)ethylamine (0.79 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 crystallized from EtOAc to provide 1.31 g (79%) 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 crystallized from EtOAc

Sources & evidence

ORD record
ord-abc121e050a345fabeae68f03bffeaad
Source dataset
uspto-grants-1998_02
Patent number
US05714503

Reaction notes

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