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Water → 7-(Cyclohexyloxy)-4,6-dinitro-2-(trifluoromethyl)-1H-benzimidazole

HRID 1974347
Notes
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Reaction equation

HRID 1974347 reaction equation
[CH:1]1([OH:7])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[K].Cl[C:10]1[C:18]2[NH:17][C:16]([C:19]([F:22])([F:21])[F:20])=[N:15][C:14]=2[C:13]([N+:23]([O-:25])=[O:24])=[CH:12][C:11]=1[N+:26]([O-:28])=[O:27].O>CN(C)P(=O)(N(C)C)N(C)C>[CH:1]1([O:7][C:10]2[C:18]3[NH:17][C:16]([C:19]([F:21])([F:22])[F:20])=[N:15][C:14]=3[C:13]([N+:23]([O-:25])=[O:24])=[CH:12][C:11]=2[N+:26]([O-:28])=[O:27])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 962WaterHCID 7966CyclohexanolHCID 5462222PotassiumHCID 1356775774-Chloro-5,7-dinitro-2-trifluoromethylbenzimidazole

Product 1

HCID 214893557-(Cyclohexyloxy)-4,6-dinitro-2-(trifluoromethyl)-1H-benzimidazole

Reagents, catalysts & solvents 1

HCID 12679
Hexamethylphosphoramide
Solvent

Procedure

Cyclohexanol (5.4 grams) and potassium (1.9 grams) were reacted in 50 milliliters of dry hexamethylphosphoric triamide. When reaction had ceased, the solution was stirred and 5 grams of 4-chloro-5,7-dinitro-2-trifluoromethylbenzimidazole were added. Stirring was continued overnight. The reaction mixture was then poured into water, acidified, and extracted with ethyl acetate. The ethyl acetate was then removed by evaporation, and the residue was chromatographed on 300 milliliters of silica gel using benzene as eluant. The benzene was removed by evaporation and the crude product was recrystallized from an aliphatic hydrocarbon fraction boiling at 60°-80° C., to which there had been added a trace of benzene. The resulting 4-cyclohexyloxy-5,7-dinitro-2-trifluoromethylbenzimidazole product melted at 151°-2° C. Its identity was confirmed by NMR and by elemental analysis.

Workup

  1. customWhen reaction
  2. stirringStirring
  3. extractionextracted with ethyl acetate
  4. customThe ethyl acetate was then removed by evaporation
  5. customthe residue was chromatographed on 300 milliliters of silica gel
  6. customThe benzene was removed by evaporation
  7. customthe crude product was recrystallized from an aliphatic hydrocarbon fraction boiling at 60°-80° C., to which there
  8. additionhad been added a trace of benzene

Sources & evidence

ORD record
ord-6e526ddb45724967a7afea5c4772a59b
Source dataset
uspto-grants-1976_12
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US04000295

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes