N,2-Dimethyl-N-[2-nitro-5-(trifluoromethyl)phenyl]propanamide → 1-Methyl-2-(propan-2-yl)-6-(trifluoromethyl)-1H-benzimidazole

HRID 1288321Notes

Reaction equation

HRID 1288321 reaction equation
[CH3:1][N:2]([C:16](=O)[CH:17]([CH3:19])[CH3:18])[C:3]1[CH:8]=[C:7]([C:9]([F:12])([F:11])[F:10])[CH:6]=[CH:5][C:4]=1[N+:13]([O-])=O>[Pd].C(O)C>[CH:17]([C:16]1[N:2]([CH3:1])[C:3]2[CH:8]=[C:7]([C:9]([F:12])([F:11])[F:10])[CH:6]=[CH:5][C:4]=2[N:13]=1)([CH3:19])[CH3:18]

Participants

4

Reactant 1

HCID 21504721N,2-Dimethyl-N-[2-nitro-5-(trifluoromethyl)phenyl]propanamide

Product 1

HCID 215047021-Methyl-2-(propan-2-yl)-6-(trifluoromethyl)-1H-benzimidazole

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

Shake 12.0 g. of N-methyl-2'-nitro-5'-trifluoromethylisobutyranilide in 100 ml. of ethanol containing 0.3 g. of 5% palladium on carbon at an initial pressure of approximately 50 lbs. per square inch. Filter, removing the solvent, and add 40 ml. of 4N hydrochloric acid and reflux for 30 minutes. Cool, and basify with sodium bicarbonate. Extract with ether and dry over sodium sulfate. Sublime at 55° C (0.1 mm) obtaining the product of this step.

Workup

  1. filtrationFilter
  2. customremoving the solvent
  3. additionadd 40 ml
  4. temperatureof 4N hydrochloric acid and reflux for 30 minutes
  5. temperatureCool
  6. extractionExtract with ether
  7. dry with materialdry over sodium sulfate
  8. customSublime at 55° C (0.1 mm) obtaining the product of this step

Sources & evidence

ORD record
ord-9962b0305907493783b4a1211cdd5ee5
Source dataset
uspto-grants-1976_10
Patent number
US03987182

Reaction notes

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