Butanal → 4-nitro-2-propyl-1H-benzoimidazole

HRID 15536

Reaction equation

HRID 15536 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([NH2:10])[C:5]=1[NH2:11])([O-:3])=[O:2].[CH:12](=O)[CH2:13][CH2:14][CH3:15].[NH4+].[OH-]>O=P(Cl)(Cl)Cl>[N+:1]([C:4]1[C:5]2[N:11]=[C:12]([CH2:13][CH2:14][CH3:15])[NH:10][C:6]=2[CH:7]=[CH:8][CH:9]=1)([O-:3])=[O:2]

Participants

5

Reactant 3

HCID 261ButanalHCID 14923Ammonium HydroxideHCID 43595253-Nitro-1,2-phenylenediamine

Product 1

HCID 107746084-nitro-2-propyl-1H-benzoimidazoleYield 87.2%

Reagents, catalysts & solvents 1

HCID 24813Phosphorus oxychlorideSolvent

Procedure

3-Nitro-benzene-1,2-diamine (1.0 g, 6.54 mmol) and butyraldehyde (630 μL, 7.19 mmol) were stirred in POCl3 (10 mL) at 85° C. for 3 hours. The reaction was cooled to ambient temperature and poured over ice. The resulting mixture was basified with NH4OH. The precipitate was filtered and washed with ice water to give 1.17 g of the sub-title compound that was used without further purification.

Workup

  1. additionpoured over ice
  2. filtrationThe precipitate was filtered
  3. washwashed with ice water

Sources & evidence

ORD record
ord-6c54cbcdd50b4c60819d061a284331fb
Source dataset
uspto-grants-2010_06
Patent number
US07732618B2

Linked notes

Loading…