Imidazole → HCID 13457306, compound

HRID 463014Notes

Reaction equation

HRID 463014 reaction equation
N1C=CN=C1.S(Cl)([Cl:8])=O.[F:10][C:11]1[CH:16]=[C:15]([F:17])[CH:14]=[CH:13][C:12]=1[C:18](O)([C:25]([F:28])([F:27])[F:26])[CH2:19][N:20]1[CH:24]=[N:23][CH:22]=[N:21]1.C(=O)(O)[O-].[Na+]>C(#N)C>[Cl:8][C:18]([C:12]1[CH:13]=[CH:14][C:15]([F:17])=[CH:16][C:11]=1[F:10])([C:25]([F:28])([F:27])[F:26])[CH2:19][N:20]1[CH:24]=[N:23][CH:22]=[N:21]1

Participants

6

Reactant 4

HCID 795ImidazoleHCID 24386Thionyl ChlorideHCID 516892Sodium BicarbonateHCID 13457296HCID 13457296, compound

Product 1

HCID 13457306HCID 13457306, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent2×

Procedure

Imidazole (0.53 g, 7.8 mmole) was dissolved in dry acetonitrile (4 ml) and thionyl chloride (0.3 ml, 4.1 mmole) was added dropwise over 2 minutes followed by a solution of 2-(2,4-difluorophenyl)-1-(1H-1,2,4-triazol-1-yl)-3,3,3-trifluoropropan-2-ol (0.389 g, 1.25 mmole) in dry acetonitrile (12 ml). The mixture was stirred at room temperature for 24 hours and then heated to 70° C. for 1/2 hour. The cooled mixture was then poured into sodium bicarbonate solution and extracted with dichloromethane (3×100 ml). The combined dichloromethane extracts were washed once with water, dried over magnesium sulphate and evaporated. Chromatography of the residue on silica (230-400 mesh), eluting with 40:60 (by volume) ethyl acetate:hexane gave, after recrystallization from ethyl acetate/hexane, the title compound, 170 mg (41%), m.p. 87°-88° C.

Workup

  1. temperatureheated to 70° C. for 1/2 hour
  2. extractionextracted with dichloromethane (3×100 ml)
  3. washThe combined dichloromethane extracts were washed once with water
  4. dry with materialdried over magnesium sulphate
  5. customevaporated
  6. washChromatography of the residue on silica (230-400 mesh), eluting with 40:60 (by volume) ethyl acetate
  7. customhexane gave
  8. customafter recrystallization from ethyl acetate/hexane

Sources & evidence

ORD record
ord-e3fdbc4e61ff40b4b076cca071d4747c
Source dataset
uspto-grants-1985_05
Patent number
US04518604

Reaction notes

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