Imidazole → Hydrochloric Acid

HRID 371176Notes

Reaction equation

HRID 371176 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][N:17]=2)(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:30])=O>C(#N)C>[ClH:1].[ClH:30].[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]([Cl:30])([C:16]2[CH:21]=[CH:20][C:19]([Cl:22])=[CH:18][N:17]=2)[CH2:9][N:10]2[CH:14]=[N:13][CH:12]=[N:11]2)=[N:6][CH:7]=1

Participants

6

Reactant 3

HCID 795ImidazoleHCID 24386Thionyl ChlorideHCID 202745161,1-bis(5-chloropyrid-2-yl)-2-(1H-1,2,4-triazol-1-yl)ethanol

Product 2

HCID 313Hydrochloric AcidHCID 202745131,1-Bis(5-chloropyrid-2-yl)-2-(1H-1,2,4-triazol-1-yl)ethyl chloride hydrochloride

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To 2.0 g (5.95 mmoles) of 1,1-bis(5-chloropyrid-2-yl)-2-(1H-1,2,4-triazol-1-yl)ethanol and 2.4 g (35.3 mmoles) of imidazole in 60 ml. of acetonitrile was added with stirring 2.1 g (17.65 mmoles) of thionyl chloride, the reaction mixture stirred for 2 hrs at room temperature and the solvent allowed to evaporate. Dilute sodium bicarbonate solution (30 ml) was added to the residue and the mixture extracted with ethyl acetate (3×50 ml). The combined extracts were dried over magnesium sulfate, concentrated to dryness and the residue chromatographed on 230-400 mesh silica gel using ethyl acetate-petrol (b.p. 60°-80° C.) (1:1, v:v) as the eluent. The fractions containing the product were combined and concentrated in vacuo to a colorless oil. Treatment of the residue with ethereal hydrogen chloride gave 1.4 (60% yield) of the desired product as a white solid, m.p. 115°-125° C.

Workup

  1. customto evaporate
  2. additionDilute sodium bicarbonate solution (30 ml) was added to the residue
  3. extractionthe mixture extracted with ethyl acetate (3×50 ml)
  4. dry with materialThe combined extracts were dried over magnesium sulfate
  5. concentrationconcentrated to dryness
  6. customthe residue chromatographed on 230-400 mesh silica gel
  7. additionThe fractions containing the product
  8. concentrationconcentrated in vacuo to a colorless oil

Sources & evidence

ORD record
ord-a5f38b363df24986a56597c5a0a3ab84
Source dataset
uspto-grants-1985_07
Patent number
US04529799

Reaction notes

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