Imidazole → HCID 433777, compound

HRID 1761941Notes

Reaction equation

HRID 1761941 reaction equation
N1[CH:5]=[CH:4]N=C1.FC(F)(F)OC1C=CC([C:15](C2C=CC(OC(F)(F)F)=CC=2)([OH:23])[CH:16]([N:18]2[N:22]=[N:21][CH:20]=[N:19]2)[CH3:17])=CC=1.S(Cl)(Cl)=[O:38].O>C(#N)C>[CH2:4]([O:38][C:15](=[O:23])[CH:16]([N:18]1[N:22]=[N:21][CH:20]=[N:19]1)[CH3:17])[CH3:5]

Participants

6

Reactant 4

HCID 795ImidazoleHCID 962WaterHCID 24386Thionyl ChlorideHCID 20042590HCID 20042590, compound

Product 1

HCID 433777HCID 433777, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of imidazole (1.23 g) and 1,1-bis(4-trifluoromethoxyphenyl)-1-hydroxy-2-(2H-tetrazol-2-yl)propane prepared as described in Example b 3 (1.34 g) in dry acetonitrile (50 ml) under an atmosphere of nitrogen, was added thionylchloride (1.07 g). A precipitate appeared and the reaction was stirred at room temperature for 5 hours. The mixture was then poured into water (100 ml) and extracted with ether (2×70 ml). The organic extracts were combined and washed well with saturated aqueous sodium bicarbonate solution (50 ml) then with water (50 ml). The organic layer was dried over anhydrous magnesium sulphate, and evaporated to give a yellow oil which was purified by h.p.l.c. on a silica gel column eluted with n-hexane/ethyl acetate (5:1) to give a colourless oil (900 mg).

Workup

  1. extractionextracted with ether (2×70 ml)
  2. washwashed well with saturated aqueous sodium bicarbonate solution (50 ml)
  3. dry with materialThe organic layer was dried over anhydrous magnesium sulphate
  4. customevaporated
  5. customto give a yellow oil which
  6. customwas purified by h.p.l.c
  7. washon a silica gel column eluted with n-hexane/ethyl acetate (5:1)

Sources & evidence

ORD record
ord-80ed38b108544eaaba6ea72d56db83f8
Source dataset
uspto-grants-1989_05
Patent number
US04829074

Reaction notes

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