Hexane → HCID 178519501, compound

HRID 261968

Reaction equation

HRID 261968 reaction equation
[CH2:1]([Li])[CH2:2][CH2:3][CH3:4].[CH3:6][CH2:7][CH2:8][CH2:9]CC.[CH2:12]([N:20]1[CH:24]=[CH:23][N:22]=C1)[CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.ClC1C=CC(C(C2C=CC=CC=2)=[O:31])=CC=1>C(OCC)C>[CH2:1]([C:23]1[N:22]=[C:12]([CH:13]([C:14]2[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=2)[OH:31])[NH:20][CH:24]=1)[CH2:2][C:3]1[CH:4]=[CH:9][CH:8]=[CH:7][CH:6]=1

Participants

6

Reactant 4

HCID 8058HexaneHCID 86534-ChlorobenzophenoneHCID 102196211-PhenethylimidazoleHCID 178418339Butyllithium

Product 1

HCID 178519501HCID 178519501, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent3×

Procedure

A solution of 20 ml. 20% butyl lithium in n-hexane (0.043 mol) in 30 ml. of diethyl ether was added dropwise under a nitrogen atmosphere to a solution of 5.5 g (0.032 mol) of 1-phenethylimidazole (J. Am. Chem. Soc., 71, 4000 (1949)) in 100 ml. of diethyl ether. After the addition was completed, the reaction mixture was stirred for another hour at room temperature. Then a solution of 7.8 g (0.036 mol) of 4-chlorobenzophenone in 75 ml. of anhydrous diethyl ether was added dropwise. The reaction mixture was stirred for 3 hours and it was then poured into 200 ml of ice-water. The ethereal layer was separated off, dried over sodium sulphate and the ether was distilled off. The residue was crystallised from a mixture of ethanol and petroleum ether (boiling range 40°-60° C.). α-(p-Chlorophenyl)-1-(phenethyl-α-phenylimidazole-2-methanol was obtained. Melting point 164°-165° C.

Workup

  1. additionAfter the addition
  2. stirringThe reaction mixture was stirred for 3 hours
  3. customThe ethereal layer was separated off
  4. dry with materialdried over sodium sulphate
  5. distillationthe ether was distilled off
  6. customThe residue was crystallised from a mixture of ethanol and petroleum ether (boiling range 40°-60° C.)

Sources & evidence

ORD record
ord-180ef7843d274bea8ebd175e969a1272
Source dataset
uspto-grants-1979_05
Patent number
US04152441

Linked notes

Loading…