Hydrochloric Acid → HCID 20274521, compound

HRID 371178Notes

Reaction equation

HRID 371178 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.S(Br)([Br:26])=O.Cl>C(#N)C.CCOCC>[ClH:1].[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]([Br:26])([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

6

Reactant 3

HCID 313Hydrochloric AcidHCID 68176Thionyl bromide2×HCID 20274524HCID 20274524, compound

Product 1

HCID 20274521HCID 20274521, compound

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6342AcetonitrileSolvent

Procedure

1-(5-Chloropyrid-2-yl)-1-(2,4-dichlorophenyl)-2-(1H-1,2,4-triazol-1-yl)ethanol (0.55 g, 1.49 mmoles) was stirred in acetonitrile (20 ml) and thionyl bromide (0.4 g, 1.92 mmoles) was added. After 1 hr. at room temperature, a small amount of starting material remained (as shown by t.l.c.) and thus a further 0.1 g of thionyl bromide was added and the solution was stirred overnight at room temperature. The acetonitrile was then removed by evaporation under reduced pressure and the residue was basified with aqueous sodium bicarbonate solution and extracted with ethyl acetate (3×40 ml). The combined organic extracts were dried over magnesium sulfate and evaporated and the residue was flash chromatographed on silica (230-400 mesh), eluting with ethyl acetate:hexane (1:3, v:v) to give an oil which was dissolved in dry ether and treated with ethereal hydrogen chloride. The white solid which precipitated (0.23 g) was recrystallized from isopropanol/diisopropyl ether to give the title compound as white crystals, 0.112 g (16%), m.p. 130° -150° C.

Workup

  1. customat room temperature
  2. customThe acetonitrile was then removed by evaporation under reduced pressure
  3. extractionextracted with ethyl acetate (3×40 ml)
  4. dry with materialThe combined organic extracts were dried over magnesium sulfate
  5. customevaporated
  6. customchromatographed on silica (230-400 mesh)
  7. washeluting with ethyl acetate:hexane (1:3, v:v)
  8. customto give an oil which
  9. customThe white solid which precipitated (0.23 g)
  10. customwas recrystallized from isopropanol/diisopropyl ether

Sources & evidence

ORD record
ord-8c586ec179a7431c9ed09fb57346ae68
Source dataset
uspto-grants-1985_07
Patent number
US04529799

Reaction notes

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