Nitric Acid → HCID 9882022, compound
Reaction equation
S(=O)(=O)(O)O.[F:6][C:7]([F:21])([F:20])[C:8]([C:11]1[NH:12][C:13]2[CH:19]=[CH:18][CH:17]=[CH:16][C:14]=2[N:15]=1)([OH:10])[CH3:9].[N+:22]([O-])([OH:24])=[O:23]>C(OCC)C>[F:21][C:7]([F:6])([F:20])[C:8]([C:11]1[NH:15][C:14]2[CH:16]=[C:17]([N+:22]([O-:24])=[O:23])[CH:18]=[CH:19][C:13]=2[N:12]=1)([OH:10])[CH3:9]Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 5 °C
Procedure
To stirred concentrated sulfuric acid (11 mL) was added 1,1,1-trifluoro-2-benzimidazol-2-ylpropan-2-ol (3.00 g) under a nitrogen atmosphere while maintaining the temperature at 5° C. The reaction mixture was treated with a nitrating reagent (3.5 mL) containing concentrated nitric acid and concentrated sulfuric acid (1.5 mL), while maintaining the reaction temperature below 35° C., and was then stirred for 1 hour at ice bath temperature. The reaction mixture was then poured onto ice, neutralized to pH 7-8, extracted with diethyl ether, and dried. The solvent was evaporated to leave a gold oil. Trituration of the oil with diethyl ether provided the title compound as a white solid (0.80 g); mp 73°-75° C., resolidified mp 173°-174° C.; NMR (250 MHz): 1.68 (s,3), 7.62 (s,1), 7.78 (broad d,1), 8.19 (dd,1), 8.52 (s,1), 13.4 (s,1); MS: m/z=276 (M+1). Analysis for C10H8F3N3O: Calculated C, 43.65; H, 2.93; N, 15.27; Found: C, 43.32; H, 3.02; N, 15.03.
Workup
- temperaturewhile maintaining the reaction temperature below 35° C.
- additionThe reaction mixture was then poured onto ice
- extractionextracted with diethyl ether
- customdried
- customThe solvent was evaporated
- customto leave a gold oil
Sources & evidence
- ORD record
- ord-dcee4f426bd74e9fbfb9f7212c36066a
- Source dataset
- uspto-grants-1996_04
- Patent number
- US05504089
Reaction notes
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