Nitric Acid → HCID 20383929, compound

HRID 1447503Notes

Reaction equation

HRID 1447503 reaction equation
S(=O)(=O)(O)O.[CH2:6]([N:8]1[C:12]2[CH:13]=[C:14]([Cl:21])[C:15]([S:17]([CH3:20])(=[O:19])=[O:18])=[CH:16][C:11]=2[N:10]=[C:9]1[CH3:22])[CH3:7].[N+:23]([O-])([OH:25])=[O:24].[OH-].[NH4+]>>[CH2:6]([N:8]1[C:12]2[C:13]([N+:23]([O-:25])=[O:24])=[C:14]([Cl:21])[C:15]([S:17]([CH3:20])(=[O:18])=[O:19])=[CH:16][C:11]=2[N:10]=[C:9]1[CH3:22])[CH3:7]

Participants

5

Reactant 4

HCID 944Nitric AcidHCID 1118Sulfuric Acid2×HCID 14923Ammonium HydroxideHCID 20383924HCID 20383924, compound

Product 1

HCID 20383929HCID 20383929, compoundYield 73.4%

Procedure

To a stirred, cooled solution of 40 ml. of concentrated sulfuric acid (at 0°-5° C.) was added, dropwise, 4.0 g. (0.015 mole) of 1-ethyl-2-methyl-5-methylsulfonyl-6-chlorobenzimidazole. Stirring was continued until all solid was in solution. To this stirred and cooled solution was added 6.0 g. (0.086 mole) of 90% fuming nitric acid, dropwise, over a 30 minute period. Stirring was continued while cooling for 9 hours and then the reaction mixture allowed to warm to room temperature over a 14 hour period. An additional 13.5 g. of 30% fuming sulfuric acid was then added, dropwise. The reaction mixture was stirred for about 24 hours and then stirred at about 40° C. for an additional 64 hours. The resultant reaction mixture was poured into a stirred mixture of 300 ml. of ice +200 ml. of concentrated ammonium hydroxide. The resultant aqueous mixture was extracted thrice with 100 ml. portions of chloroform and the combined chloroform extracts dried over anhydrous sodium sulfate. The resultant chloroform solution was evaporated to dryness under reduced pressure to give 3.04 g. (73.4%) of the desired product, melting at 75°-79° C.

Workup

  1. temperatureTo a stirred, cooled solution of 40 ml
  2. stirringTo this stirred
  3. temperaturecooled solution
  4. additionwas added 6.0 g
  5. stirringStirring
  6. temperaturewhile cooling for 9 hours
  7. stirringThe reaction mixture was stirred for about 24 hours
  8. stirringstirred at about 40° C. for an additional 64 hours
  9. customThe resultant reaction mixture
  10. additionwas poured into a stirred mixture of 300 ml
  11. extractionThe resultant aqueous mixture was extracted thrice with 100 ml
  12. dry with materialportions of chloroform and the combined chloroform extracts dried over anhydrous sodium sulfate
  13. customThe resultant chloroform solution was evaporated to dryness under reduced pressure
  14. customto give 3.04 g

Sources & evidence

ORD record
ord-d5a6e01557a24164a5874e57f32995d1
Source dataset
uspto-grants-1979_12
Patent number
US04177057

Reaction notes

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