Nitric Acid → HCID 70501161, compound

HRID 1995068Notes

Reaction equation

HRID 1995068 reaction equation
[Cl:1][C:2]1[CH:15]=[C:14]([Cl:16])[CH:13]=[CH:12][C:3]=1[CH:4]([OH:11])[CH2:5][N:6]1[CH:10]=[CH:9][N:8]=[CH:7]1.[H-].[Na+].Br[CH2:20][C:21]1[C:25]2[C:26]([Cl:31])=[CH:27][C:28]([Cl:30])=[CH:29][C:24]=2[O:23][CH:22]=1.[Cl-].[Na+].[N+:34]([O-:37])([OH:36])=[O:35]>CN(C)C=O.C(OCC)C.C(OCC)(=O)C.C(O)(=O)C.O>[N+:34]([O-:37])([OH:36])=[O:35].[Cl:1][C:2]1[CH:15]=[C:14]([Cl:16])[CH:13]=[CH:12][C:3]=1[CH:4]([O:11][CH2:20][C:21]1[C:25]2[C:26]([Cl:31])=[CH:27][C:28]([Cl:30])=[CH:29][C:24]=2[O:23][CH:22]=1)[CH2:5][N:6]1[CH:10]=[CH:9][N:8]=[CH:7]1

Participants

11

Reactant 5

HCID 944Nitric AcidHCID 5234Sodium ChlorideHCID 24758Sodium hydrideHCID 32238(+-)-alpha-(2,4-Dichlorophenyl)-1H-imidazole-1-ethanolHCID 20489646HCID 20489646, compound

Product 1

HCID 70501161HCID 70501161, compound

Reagents, catalysts & solvents 5

HCID 176Acetic AcidSolventHCID 962WaterSolventHCID 3283Diethyl EtherSolventHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

A stirred solution of 0.51 g (0.002 mol) of 2,4-dichloro-α-[(1-imidazolyl)methyl]benzyl alcohol was cooled to 0° C. and treated with 48 mg (0.002 mol) of sodium hydride (60 mg of an 80% dispersion in mineral oil). Stirring was continued and, after the effervescence had ceased (about 0.5 hour), the mixture was treated with a solution of 0.56 g (0.002 mol) of 3-bromomethyl-4,6-dichlorobenzofuran in 2 ml of dry dimethylformamide. The mixture was stirred at 0° C. for 0.5 hour and then at room temperature for 2 hours. The mixture was treated with 50 ml of water containing 0.5 ml of glacial acetic acid and then saturated with sodium chloride. The product was extracted with three 30 ml portions of ethyl acetate. The combined ethyl acetate extracts were washed with brine, dried over sodium sulphate and evaporated at 30° C./12 mmHg to give a pale brown viscous oil. This oil was dissolved in 15 ml of dry diethyl ether by the addition of the minimum volume of ethyl acetate and treated with 0.2 ml of concentrated nitric acid. The precipitated product was crystallised from ethanol to yield 0.57 g of 1-[2,4-dichloro-β-[(4,6-dichlorobenzofuran-3-yl)methoxy]-phenethyl]imidazole nitrate of melting point 105° C.

Workup

  1. custom(about 0.5 hour)
  2. stirringThe mixture was stirred at 0° C. for 0.5 hour
  3. extractionThe product was extracted with three 30 ml portions of ethyl acetate
  4. washThe combined ethyl acetate extracts were washed with brine
  5. dry with materialdried over sodium sulphate
  6. customevaporated at 30° C./12 mmHg
  7. customto give a pale brown viscous oil
  8. customThe precipitated product was crystallised from ethanol

Sources & evidence

ORD record
ord-67e32881d11243c2a2ff299bc9249f9c
Source dataset
uspto-grants-1983_09
Patent number
US04402968

Reaction notes

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