Imidazole → HCID 14538177, compound

HRID 2108272Notes

Reaction equation

HRID 2108272 reaction equation
S(Cl)([Cl:3])=O.[O:5]([C:12]1[CH:13]=[C:14]([CH:33]=[CH:34][CH:35]=1)[CH2:15][S:16][CH2:17][C:18]([C:24]1[CH:29]=[CH:28][C:27]([O:30][CH2:31][CH3:32])=[CH:26][CH:25]=1)(O)[C:19]([F:22])([F:21])[F:20])[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1.N1C=CN=C1.C(=O)(O)[O-].[Na+]>C(#N)C>[O:5]([C:12]1[CH:13]=[C:14]([CH:33]=[CH:34][CH:35]=1)[CH2:15][S:16][CH2:17][C:18]([Cl:3])([C:24]1[CH:29]=[CH:28][C:27]([O:30][CH2:31][CH3:32])=[CH:26][CH:25]=1)[C:19]([F:22])([F:21])[F:20])[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1

Participants

6

Reactant 4

HCID 795ImidazoleHCID 24386Thionyl ChlorideHCID 516892Sodium BicarbonateHCID 14538205HCID 14538205, compound

Product 1

HCID 14538177HCID 14538177, compoundYield 69.9%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
0 °C

Procedure

Thionyl chloride (0.2 g) was added to a cooled solution of 1,1,1-trifluoro-2-(4-ethoxyphenyl)-2-hydroxyprop-3-yl 3-phenoxybenzyl sulphide (0.165 g) and imidazole (0.123 g) in acetonitrile (5 cm3), the temperature of the mixture being maintained at 0° C. The reaction mixture was then allowed to warm to the ambient temperature (21° C.) and stirred for 30 minutes, before being added to a saturated aqueous solution of sodium bicarbonate (7 cm3). The product was extracted into diethyl ether (3×15 cm3), and the combined organic layers were dried over anhydrous magnesium sulphate and evaporated under reduced pressure. The residue was purified by chromatography on a silica gel support, eluting with petroleum ether containing 10% by volume diethy ether, to give 1,1,1-trifluoro-2-chloro-2-(4-ethoxyphenyl)prop-3-yl 3-phenoxybenzyl sulphide (0.12 g) as a colourless oil.

Workup

  1. temperatureto warm to the ambient temperature (21° C.)
  2. extractionThe product was extracted into diethyl ether (3×15 cm3)
  3. dry with materialthe combined organic layers were dried over anhydrous magnesium sulphate
  4. customevaporated under reduced pressure
  5. customThe residue was purified by chromatography on a silica gel support
  6. washeluting with petroleum ether containing 10% by volume diethy ether

Sources & evidence

ORD record
ord-22c0ee71efec4239925b445bc1e9d2ed
Source dataset
uspto-grants-1990_06
Patent number
US04937388

Reaction notes

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