Water → 4-Propylamino-7-nitro-2,5-bis(trifluoromethyl)benzimidazole

HRID 1578718Notes

Reaction equation

HRID 1578718 reaction equation
Cl[C:2]1[C:10]2[NH:9][C:8]([C:11]([F:14])([F:13])[F:12])=[N:7][C:6]=2[C:5]([N+:15]([O-:17])=[O:16])=[CH:4][C:3]=1[C:18]([F:21])([F:20])[F:19].[CH2:22]([NH2:25])[CH2:23][CH3:24].C(N(CC)CC)C.O>C(O)C>[CH2:22]([NH:25][C:2]1[C:10]2[NH:9][C:8]([C:11]([F:14])([F:13])[F:12])=[N:7][C:6]=2[C:5]([N+:15]([O-:17])=[O:16])=[CH:4][C:3]=1[C:18]([F:21])([F:20])[F:19])[CH2:23][CH3:24]

Participants

6

Reactant 4

HCID 962WaterHCID 7852PropylamineHCID 8471TriethylamineHCID 1355549354-Chloro-7-nitro-2,5-bis(trifluoromethyl)benzimidazole

Product 1

HCID 1357839314-Propylamino-7-nitro-2,5-bis(trifluoromethyl)benzimidazole

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

4-Chloro-7-nitro-2,5-bis(trifluoromethyl)benzimidazole (2.2 grams), propylamine (0.39 gram), and excess triethylamine were mixed in about 50 milliliters of ethanol. The reaction mixture was heated to reflux and refluxed over a weekend (about 60 hours). The reaction mixture was then poured into water and acidified. The desired 4-propylamino-7-nitro-2,5-bis(trifluoromethyl)benzimidazole product precipitated and was separated by filtration. After recrystallization from a mixture of ethanol and water, the compound melted at 129°-31°C. Analysis, Calc.: C, 40.4; H, 2.81; N, 15.73 Found: C, 40.5; H, 2.78; N, 15.51

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureto reflux
  3. temperaturerefluxed over a weekend (about 60 hours)
  4. customThe desired 4-propylamino-7-nitro-2,5-bis(trifluoromethyl)benzimidazole product precipitated
  5. customwas separated by filtration
  6. customAfter recrystallization
  7. additionfrom a mixture of ethanol and water

Sources & evidence

ORD record
ord-99ac0c34a2cc46c0b87465e02d190b99
Source dataset
uspto-grants-1976_02
Patent number
US03939166

Reaction notes

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