Imidazole → HCID 66617618, compound

HRID 72319Notes

Reaction equation

HRID 72319 reaction equation
[OH:1][CH2:2][C:3]1[O:7][N:6]=[C:5]([C:8]2[CH:13]=[CH:12][C:11]([OH:14])=[CH:10][CH:9]=2)[CH:4]=1.Br[CH2:16][CH2:17][Cl:18].[NH:19]1[CH:23]=[CH:22][N:21]=[CH:20]1.C(=O)([O-])[O-].[K+].[K+]>C(#N)C>[Cl:18][CH2:17][CH2:16][O:14][C:11]1[CH:12]=[CH:13][C:8]([C:5]2[CH:4]=[C:3]([CH2:2][OH:1])[O:7][N:6]=2)=[CH:9][CH:10]=1.[N:19]1([CH2:16][CH2:17][O:14][C:11]2[CH:12]=[CH:13][C:8]([C:5]3[CH:4]=[C:3]([CH2:2][OH:1])[O:7][N:6]=3)=[CH:9][CH:10]=2)[CH:23]=[CH:22][N:21]=[CH:20]1

Participants

7

Reactant 4

HCID 795ImidazoleHCID 78491-Bromo-2-ChloroethaneHCID 11430Potassium CarbonateHCID 136359908HCID 136359908, compound

Product 2

HCID 66617618HCID 66617618, compoundHCID 66617668{3-[4-(2-Chloro-ethoxy)-phenyl]-isoxazol-5-yl}-methanol

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

{3-[4-(2-chloro-ethoxy)-phenyl]-isoxazol-5-yl}-methanol was synthesized using 4-(5-hydroxymethyl-isoxazol-3-yl)-phenol and 2-bromo-1-chloroethane in the same manner as in Example 10, and then 2 equivalents of imidazole and 3 equivalents of potassium carbonate were added to the compound and refluxed with acetonitrile. After 12 hours of the reaction, the solvent was dried under reduced pressure and purified by column chromatography to obtain {3-[4-(2-imidazol-1-yl-ethoxy)-phenyl]-isoxazol-5-yl}-methanol. A carbamoylation of the compound was performed in the same manner as in Example 1-3 to obtain carbamic acid 3-[4-(2-imidazol-1-yl-ethoxy)-phenyl]-isoxazol-5-ylmethyl ester as a desired compound.

Workup

  1. customAfter 12 hours of the reaction
  2. customthe solvent was dried under reduced pressure
  3. custompurified by column chromatography

Sources & evidence

ORD record
ord-ab28aebb8f4b45a4bb26e7efa13a4c4c
Source dataset
uspto-grants-2014_09
Patent number
US08828992B2

Reaction notes

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