Acetic Acid → 2-(5-acetylthiophen-2-yl)-1H-benzimidazole-4-carboxamide

HRID 2374677Notes

Reaction equation

HRID 2374677 reaction equation
[NH2:1][C:2]1[C:7]([C:8](=[O:10])[NH2:9])=[CH:6][CH:5]=[CH:4][C:3]=1[NH:11][C:12]([C:14]1[S:15][C:16]([C:19](=[O:21])[CH3:20])=[CH:17][CH:18]=1)=O.C(O)(=O)C>CN(C)C=O>[C:19]([C:16]1[S:15][C:14]([C:12]2[NH:11][C:3]3[CH:4]=[CH:5][CH:6]=[C:7]([C:8]([NH2:9])=[O:10])[C:2]=3[N:1]=2)=[CH:18][CH:17]=1)(=[O:21])[CH3:20]

Participants

4

Reactant 2

HCID 176Acetic AcidHCID 673537955-Acetylthiophene-2-carboxylic acid (2-amino-3-carbamoylphenyl)amide

Product 1

HCID 673520322-(5-acetylthiophen-2-yl)-1H-benzimidazole-4-carboxamideYield 95.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
125 °C

Procedure

To a solution of EXAMPLE 6A (1.70 g) in hot N,N-dimethylformamide (60 mL) was added acetic acid (50 mL) and the solution heated at 125° C. for 3 hours. After cooling, the resulting yellow solid was collected by filtration, washed with methanol and dried to give the title compound (1.52 g, 95%). MS (APCI): 286 (M+1)+.

Workup

  1. temperatureAfter cooling
  2. filtrationthe resulting yellow solid was collected by filtration
  3. washwashed with methanol
  4. customdried

Sources & evidence

ORD record
ord-9d230c6fccc441b4afd3f8ab118776b8
Source dataset
uspto-grants-2008_12
Patent number
US07462724B2

Reaction notes

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