Nitric Acid → HCID 21540596, compound

HRID 1075724Notes

Reaction equation

HRID 1075724 reaction equation
[Cl:1][C:2]1[C:3]([C:14]([F:17])([F:16])[F:15])=[CH:4][C:5]2[N:9]=[C:8]([CH3:10])[N:7]([CH2:11][CH3:12])[C:6]=2[CH:13]=1.S(=O)(=O)(O)O.[N+:23]([O-])([OH:25])=[O:24]>C(Cl)(Cl)Cl>[Cl:1][C:2]1[C:3]([C:14]([F:17])([F:15])[F:16])=[CH:4][C:5]2[N:9]=[C:8]([CH3:10])[N:7]([CH2:11][CH3:12])[C:6]=2[C:13]=1[N+:23]([O-:25])=[O:24]

Participants

5

Reactant 3

HCID 944Nitric AcidHCID 1118Sulfuric AcidHCID 744341H-Benzimidazole, 6-chloro-1-ethyl-2-methyl-5-(trifluoromethyl)-

Product 1

HCID 21540596HCID 21540596, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of 11.0g. (0.04 mole) of 6-chloro-1-ethyl-2-methyl-5-trifluoromethylbenzimidazole dissolved in 110 ml. of concentrated sulfuric acid was added 11 ml. of 90% fuming nitric acid while cooling with an ice bath. The addition required 3 hours and the resulting red-brown solution was stirred for 6 hours at 0°C. and then at room temperature for 2.5 days. After pouring onto ice, the product was precipitated by the addition of 350 ml. of concentrated ammonium hydroxide. The crude solid was isolated and dissolved in 300 ml. of chloroform. The chloroform solution was washed with water, dried over Na2SO4, filtered, and the filtrate evaporated. Crystallization of the residual solid from hexane --CCl4 (3:1) gave 9.0g. (70%) of reddish solid, m.p. 114°-116°C., whose nuclear magnetic resonance pattern confirmed it to be the desired product.

Workup

  1. temperaturewhile cooling with an ice bath
  2. additionThe addition required 3 hours
  3. waitat room temperature for 2.5 days
  4. additionAfter pouring onto ice
  5. customthe product was precipitated by the addition of 350 ml
  6. customThe crude solid was isolated
  7. dissolutiondissolved in 300 ml
  8. washThe chloroform solution was washed with water
  9. dry with materialdried over Na2SO4
  10. filtrationfiltered
  11. customthe filtrate evaporated
  12. customCrystallization of the residual solid from hexane --CCl4 (3:1)
  13. customgave 9.0g

Sources & evidence

ORD record
ord-c47fa39897a345659e092c29cb913a91
Source dataset
uspto-grants-1976_05
Patent number
US03954438

Reaction notes

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