Ammonia → (4-chlorophenyl)(1H-imidazol-2-yl)phenylmethanol

HRID 261933

Reaction equation

HRID 261933 reaction equation
[C:1]([C:9]1[NH:10][CH:11]=[CH:12][N:13]=1)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Mg].Br[C:16]1[CH:21]=[CH:20][C:19]([Cl:22])=[CH:18][CH:17]=1.Cl.N>O1CCCC1>[Cl:22][C:19]1[CH:20]=[CH:21][C:16]([C:1]([C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)([C:9]2[NH:13][CH:12]=[CH:11][N:10]=2)[OH:8])=[CH:17][CH:18]=1

Participants

7

Reactant 5

HCID 222AmmoniaHCID 313Hydrochloric AcidHCID 7806p-BromochlorobenzeneHCID 1861972-benzoyl-1H-imidazoleHCID 5462224Magnesium

Product 1

HCID 12433863(4-chlorophenyl)(1H-imidazol-2-yl)phenylmethanol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of 17.2 g. of 2-benzoylimidazole (A. Sonn and P. Greif, Ber. 66 (1933), 1900) in 100 ml. of anhydrous tetrahydrofuran was added drop-wise to a Grignard reagent prepared from 5.8 g. of magnesium and 45.9 g. of 1-bromo-4-chlorobenzene in 150 ml. of anhydrous tetrahydrofuran. The reaction mixture was boiled under reflux for half an hour, cooled and poured onto a mixture of ice and hydrochloric acid. The solution was neutralized with concentrated ammonia solution and extracted with tetrahydrofuran. The organic solvents layer was dried and concentrated; the residue was crystallised from isopropyl alcohol. Melting point of the product was 162°-165° C.

Workup

  1. customprepared from 5.8 g
  2. temperatureunder reflux for half an hour
  3. temperaturecooled
  4. extractionextracted with tetrahydrofuran
  5. customThe organic solvents layer was dried
  6. concentrationconcentrated
  7. customthe residue was crystallised from isopropyl alcohol
  8. customwas 162°-165° C.

Sources & evidence

ORD record
ord-71eb54f9480e4b70b1eebfd720c4d52a
Source dataset
uspto-grants-1979_05
Patent number
US04152441

Linked notes

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