Nitric Acid → HCID 178487855, compound

HRID 1458421Notes

Reaction equation

HRID 1458421 reaction equation
[CH:1]([C:4]1[NH:5][C:6]2[CH:12]=[C:11]([O:13][CH3:14])[CH:10]=[CH:9][C:7]=2[N:8]=1)([CH3:3])[CH3:2].[N+:15]([O-])([OH:17])=[O:16].CO.C(Cl)Cl>C(O)(C(F)(F)F)=O>[CH:1]([C:4]1[NH:5][C:6]2[C:12]([N+:15]([O-:17])=[O:16])=[C:11]([O:13][CH3:14])[CH:10]=[CH:9][C:7]=2[N:8]=1)([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 944Nitric AcidHCID 4162829HCID 4162829, compoundHCID 21226129Dichloromethane methanol

Product 1

HCID 178487855HCID 178487855, compound

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

2-Isopropyl-5-methoxybenzimidazole (50 g) was dissolved in 150 mL TFA and to the mixture was added 5 mL 90% nitric acid. The reaction was stirred overnight, and the solvents removed in vacuo and the residue neutralized to pH 7 with saturated aqueous sodium bicarbonate. The residue was extracted with ethyl acetate (4×100 mL). The combined ethyl acetate fractions were dried over sodium sulfate and concentrated to give a dark residue. Chromatography (3% methanol/methylene chloride) gave 2-isopropyl-4-nitro-5-methoxybenzimidazole as a yellow solid, 24 g. Also obtained was 25 g of 2-isopropyl-5-nitro-6-methoxybenzimidazole.

Workup

  1. customthe solvents removed in vacuo
  2. extractionThe residue was extracted with ethyl acetate (4×100 mL)
  3. dry with materialThe combined ethyl acetate fractions were dried over sodium sulfate
  4. concentrationconcentrated
  5. customto give a dark residue

Sources & evidence

ORD record
ord-1ca83d4bb85e4fc4a9c4b5715e205571
Source dataset
uspto-grants-1998_12
Patent number
US05849759

Reaction notes

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