Nitric Acid → 1-[6-(2,6-Dichlorobenzyloxy)tetrahydropyran-2-ylmethyl]imidazole

HRID 905060Notes

Reaction equation

HRID 905060 reaction equation
[N+]([O-])(O)=O.[Cl:5][C:6]1[CH:25]=[CH:24][CH:23]=[C:22]([Cl:26])[C:7]=1[CH2:8][O:9][C@@H:10]1[O:15][C@@H:14]([CH2:16][N:17]2[CH:21]=[CH:20][N:19]=[CH:18]2)[CH2:13][CH2:12][CH2:11]1>C(OCC)C>[Cl:26][C:22]1[CH:23]=[CH:24][CH:25]=[C:6]([Cl:5])[C:7]=1[CH2:8][O:9][CH:10]1[O:15][CH:14]([CH2:16][N:17]2[CH:21]=[CH:20][N:19]=[CH:18]2)[CH2:13][CH2:12][CH2:11]1

Participants

4

Reactant 2

HCID 944Nitric AcidHCID 13261936Trans-1-[6-(2,6-dichlorobenzyloxy)tetrahydropyran-2-ylmethyl]imidazole

Product 1

HCID 132619351-[6-(2,6-Dichlorobenzyloxy)tetrahydropyran-2-ylmethyl]imidazoleYield 97,803.5%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

When 0.2 ml of 69% w/v aqueous nitric acid was added to a solution of 865 mg of trans-1-[6-(2,6-dichlorobenzyloxy)tetrahydropyran-2-ylmethyl]imidazole in 10 ml of diethyl ether, the solution became turbid and an oily layer separated. After decanting off the ethereal layer, more diethyl ether was added to the residue to aid crystallization and the precipitated crystals were filtered, to give 846 g of the title product. Further recrystallization of these crystals from a mixture of acetone and ethyl acetate gave the title product in the form of colourless crystals melting at 117° C.

Workup

  1. customan oily layer separated
  2. customAfter decanting off the ethereal layer, more diethyl ether
  3. additionwas added to the residue
  4. customcrystallization
  5. filtrationthe precipitated crystals were filtered

Sources & evidence

ORD record
ord-2517b7ac3b3f447fb56f3e737aff67b6
Source dataset
uspto-grants-1983_12
Patent number
US04421758

Reaction notes

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