HCID 23325448, compound → HCID 13228944, compound

HRID 1380554Notes

Reaction equation

HRID 1380554 reaction equation
C([O:8][C:9]1[CH:24]=[CH:23][C:12]([CH2:13][N:14]2[C:18]([CH2:19][C:20]#[N:21])=[C:17]([Cl:22])[N:16]=[CH:15]2)=[CH:11][C:10]=1[CH3:25])C1C=CC=CC=1>FC(F)(F)C(O)=O>[Cl:22][C:17]1[N:16]=[C:15]([C:9]2[CH:24]=[CH:23][CH:12]=[CH:11][CH:10]=2)[N:14]([CH2:13][C:12]2[CH:23]=[CH:24][C:9]([OH:8])=[C:10]([CH3:25])[CH:11]=2)[C:18]=1[CH2:19][C:20]#[N:21]

Participants

3

Reactant 1

HCID 23325448HCID 23325448, compound

Product 1

HCID 13228944HCID 13228944, compoundYield 77.1%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

1-(4-Benzyloxy-3-methylbenzyl)-4-chloro-5-cyanomethylimidazole (10 g) was boiled in 100 ml of trifluoroacetic acid for 15 minutes. The reaction mixture was then evaporated to dryness and the residue was chromatographed on a column of silica gel (100 g) using chloroform as an eluent. The desired fractions were combined and concentrated to about 20 ml to give 3.7 g of 4-chloro-5-cyanomethyl-1-(4-hydroxy-3-methylbenzyl)-2-phenylimidazole as colorless prisms, m.p. 194°-196° C.

Workup

  1. customThe reaction mixture was then evaporated to dryness
  2. customthe residue was chromatographed on a column of silica gel (100 g)
  3. concentrationconcentrated to about 20 ml

Sources & evidence

ORD record
ord-903c2c25f33b442b8e15083a598ccf02
Source dataset
uspto-grants-1986_04
Patent number
US04582847

Reaction notes

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