Chloroform → HCID 178526752, compound

HRID 437405Notes

Reaction equation

HRID 437405 reaction equation
CO[N:3]1[C:7]2[CH:8]=[C:9]([N+:15]([O-:17])=[O:16])[CH:10]=[C:11]([N+:12]([O-:14])=[O:13])[C:6]=2[N:5]=[C:4]1[C:18]([F:21])([F:20])[F:19].[NH:22]1[CH2:27][CH2:26][CH2:25][CH2:24][CH2:23]1.C(Cl)(Cl)Cl>CO>[N+:12]([C:11]1[C:6]2[NH:5][C:4]([C:18]([F:21])([F:20])[F:19])=[N:3][C:7]=2[C:8]([N:22]2[CH2:27][CH2:26][CH2:25][CH2:24][CH2:23]2)=[C:9]([N+:15]([O-:17])=[O:16])[CH:10]=1)([O-:14])=[O:13]

Participants

5

Reactant 3

HCID 6212ChloroformHCID 8082PiperidineHCID 21428399HCID 21428399, compound

Product 1

HCID 178526752HCID 178526752, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A 450 mg. portion of 1-methoxy-4,6-dinitro-2-(trifluoromethyl) benzimidazol was dissolved in methanol, and 150mg. of piperidine was added at room temperature. The reaction mixture was constantly stirred, and the progress of the reaction was monitored by thin-layer chromatography. After about 3 hours, the solvent was evaporated under vaccum, and the residue was taken up in water and acidified to pH 3. The mixture was then extracted with ethyl acetate, and the product was isolated by chromatography of the organic layer, using chloroform as the eluent. The product was recrystallized from ethanol-water, and was identified as 4,6-dinitro-7-piperidino-2-(trifluoromethyl) benzimidazole, m.p. 207° -209° C., by nuclear magnetic resonance analysis and elemental microanalysis, the results of which follow. The yield was about 70 mg.

Workup

  1. customthe solvent was evaporated under vaccum
  2. extractionThe mixture was then extracted with ethyl acetate
  3. customthe product was isolated by chromatography of the organic layer
  4. customThe product was recrystallized from ethanol-water
  5. customthe results of which

Sources & evidence

ORD record
ord-74f917bb172c44b2bf23e2a064569ef8
Source dataset
uspto-grants-1977_06
Patent number
US04031107

Reaction notes

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