Ethanol → 4-tert-BUTYLAMINO-5,7-DINITRO-2-TRIFLUOROMETHYLBENZIMIDAZOLE

HRID 1974344Notes

Reaction equation

HRID 1974344 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[N+:18]([O-:20])=[O:19].C(N(CC)CC)C.[C:28]([NH2:32])([CH3:31])([CH3:30])[CH3:29].C(O)C>O>[C:28]([NH:32][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[N+:18]([O-:20])=[O:19])([CH3:31])([CH3:30])[CH3:29]

Participants

6

Reactant 4

HCID 702EthanolHCID 6385Tert-ButylamineHCID 8471TriethylamineHCID 1356775774-Chloro-5,7-dinitro-2-trifluoromethylbenzimidazole

Product 1

HCID 1356775754-tert-BUTYLAMINO-5,7-DINITRO-2-TRIFLUOROMETHYLBENZIMIDAZOLE

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

4-Chloro-5,7-dinitro-2-trifluoromethylbenzimidazole (5.0 grams) was mixed with 1.6 grams of triethylamine and 1.2 grams of tert-butylamine in a small amount of ethanol. The resulting reaction mixture was refluxed over a weekend, then poured into water and the resulting aqueous mixture acidified and filtered to separate the expected 4-tert-butylamino-5,7-dinitro-2-trifluoromethylbenzimidazole product. It was recrystallized from ethanol as an orange solid, m.p., 195°-97° C. Elemental analysis confirmed the identity of the product. A second crop melted at 177°-88° C.

Workup

  1. customThe resulting reaction mixture
  2. temperaturewas refluxed over a weekend
  3. filtrationfiltered
  4. customto separate the expected 4-tert-butylamino-5,7-dinitro-2-trifluoromethylbenzimidazole product
  5. customIt was recrystallized from ethanol as an orange solid
  6. custom195°-97° C

Sources & evidence

ORD record
ord-19368ad923994039bfe5a79c863c667f
Source dataset
uspto-grants-1976_12
Patent number
US04000295

Reaction notes

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