Ethyl Acetate → HCID 54093329, compound

HRID 2257787Notes

Reaction equation

HRID 2257787 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][CH:22]=[CH:21][C:20]=1CCN.C(OCC)(=O)C>CN(C)C=O>[Cl:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=1[CH2:16][CH2:17][NH:13][C:11]([NH:10][C:2]1[NH:1][C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=1)=[S:12]

Participants

5

Reactant 3

HCID 8857Ethyl AcetateHCID 831172-(2-Chlorophenyl)ethylamineHCID 19704123N-(1H-benzo[d]imidazol-2-yl)-1H-imidazole-1-carbothioamide

Product 1

HCID 54093329HCID 54093329, compoundYield 40.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 1-[(2-benzimidazolyl)thiocarbamoyl]imidazole (1.22 g, 5.0 mmol) and 2-(2-chlorophenyl)ethylamine (0.81 g, 5.0 mmol) in 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 0.67 g (40%) of the titled product as a white solid: mp 166°-169° C.; IR (KBr, cm-1) 3235, 1656, 1554, 1459, 1248, 1224, 1192, 754, 737, 629; 1H NMR (300 MHz, DMSO-d6) δ 11.95 (br s, 1H), 10.82 (br s, 1H), 7.42 (m, 5H), 7.25 (m, 2H), 7.12 (m, 2H), 3.83 (m, 2H), 3.05 (t, J=7 Hz, 2H); MS (FD) m/e 330 (M+); UV (EtOH) 301 nm (ε=18044), 293 nm (ε=18559), 266 nm (ε=11113), 260 nm (ε=10441), 239 nm (ε=8428), 206 nm (ε=27620).

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-cabe090722d542339de00a04076830b9
Source dataset
uspto-grants-1997_08
Patent number
US05658907

Reaction notes

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