Imidazole → HCID 20274517, compound

HRID 371177Notes

Reaction equation

HRID 371177 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]([C:16]2[CH:21]=[CH:20][C:19]([Cl:22])=[CH:18][C:17]=2[Cl:23])(O)[CH2:9][N:10]2[CH:14]=[N:13][CH:12]=[N:11]2)=[N:6][CH:7]=1.N1C=CN=C1.S(Cl)([Cl:31])=O>C(#N)C>[ClH:1].[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]([Cl:31])([C:16]2[CH:21]=[CH:20][C:19]([Cl:22])=[CH:18][C:17]=2[Cl:23])[CH2:9][N:10]2[CH:14]=[N:13][CH:12]=[N:11]2)=[N:6][CH:7]=1

Participants

5

Reactant 3

HCID 795ImidazoleHCID 24386Thionyl ChlorideHCID 20274524HCID 20274524, compound

Product 1

HCID 20274517HCID 20274517, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

1-(5-Chloropyrid-2-yl)-1-(2,4-dichlorophenyl)-2-(1H-1,2,4-triazol-1-yl)ethanol (750 mg, 2.03 mmoles) and imidazole (840 mg, 12.35 mmoles) were stirred in 30 ml of acetonitrile while 720 mg of thionyl chloride was added. The reaction mixture was stirred for 18 hrs. at room temperature and the solvent was then evaporated. Dilute sodium bicarbonate solution (10 ml) was added to the residue and the mixture extracted with ethyl acetate (4×20 ml). The combined extracts were dried over magnesium sulfate, evaporated under vacuum and the residue chromatographed on 230-400 mesh silica gel using ethyl acetate-petrol (b.p. 60°-80° C.) (1:1, v:v). The fractions containing the product were combined and concentrated to dryness to give the product as a colorless gum. Treatment of the residue with ethereal hydrogen chloride gave the hydrochloride salt which was recrystallized from methanol-diisopropyl ether, 240 mg (28% yield), m.p. 120°-140° C.

Workup

  1. additionwas added
  2. customat room temperature and the solvent was then evaporated
  3. additionDilute sodium bicarbonate solution (10 ml) was added to the residue
  4. extractionthe mixture extracted with ethyl acetate (4×20 ml)
  5. dry with materialThe combined extracts were dried over magnesium sulfate
  6. customevaporated under vacuum
  7. customthe residue chromatographed on 230-400 mesh silica gel
  8. additionThe fractions containing the product
  9. concentrationconcentrated to dryness

Sources & evidence

ORD record
ord-51ce847ad457479d893b581cac14d998
Source dataset
uspto-grants-1985_07
Patent number
US04529799

Reaction notes

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