Nitric Acid → 1-Methyl-6-nitro-2-(propan-2-yl)-5-(trifluoromethyl)-1H-benzimidazole

HRID 1288323Notes

Reaction equation

HRID 1288323 reaction equation
[N+:1]([O-:4])(O)=[O:2].S(=O)(=O)(O)O.[CH:10]([C:13]1[N:17]([CH3:18])[C:16]2[CH:19]=[CH:20][C:21]([C:23]([F:26])([F:25])[F:24])=[CH:22][C:15]=2[N:14]=1)([CH3:12])[CH3:11].[OH-].[Na+].C(=O)([O-])[O-].[Na+].[Na+]>>[CH:10]([C:13]1[N:17]([CH3:18])[C:16]2[CH:19]=[C:20]([N+:1]([O-:4])=[O:2])[C:21]([C:23]([F:25])([F:26])[F:24])=[CH:22][C:15]=2[N:14]=1)([CH3:12])[CH3:11]

Participants

6

Reactant 5

HCID 944Nitric AcidHCID 1118Sulfuric AcidHCID 10340Sodium CarbonateHCID 14798Sodium HydroxideHCID 215047001-Methyl-2-(propan-2-yl)-5-(trifluoromethyl)-1H-benzimidazole

Product 1

HCID 215047051-Methyl-6-nitro-2-(propan-2-yl)-5-(trifluoromethyl)-1H-benzimidazole

Procedure

Slowly add 1.01 g. of 90% nitric acid dissolved in 2.2 ml. of concentrated sulfuric acid to a stirred solution of 3.00 g. of 2-isopropyl-1-methyl-5-trifluoromethylbenzimidazole in 13.2 ml. of concentrated sulfuric at about 5° C. Maintain the reaction at about 5° C for 2 hours. Pour the reaction mixture into 300 ml. of ice water and basify with 26 ml. of 50% sodium hydroxide followed by sodium carbonate. Extract with ether, dry over sodium sulfate and evaporate to dryness. Recrystallize from dichloromethane-hexane, obtaining the product of this example.

Workup

  1. customat about 5° C
  2. temperatureMaintain
  3. customthe reaction at about 5° C for 2 hours
  4. additionPour the reaction mixture into 300 ml
  5. extractionExtract with ether
  6. dry with materialdry over sodium sulfate
  7. customevaporate to dryness
  8. customRecrystallize from dichloromethane-hexane
  9. customobtaining the product of this example

Sources & evidence

ORD record
ord-587e105013884d529c5450908778d9c1
Source dataset
uspto-grants-1976_10
Patent number
US03987182

Reaction notes

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