Picric Acid → 1-Allyl-alpha-(p-chlorophenyl)-alpha-phenylimidazole-2-methanol

HRID 261964

Reaction equation

HRID 261964 reaction equation
[CH2:1](Br)[CH:2]=[CH2:3].[Cl:5][C:6]1[CH:11]=[CH:10][C:9]([C:12]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)([C:14]2[NH:15][CH:16]=[CH:17][N:18]=2)[OH:13])=[CH:8][CH:7]=1.[OH-].[Na+].C1(C(O)=C([N+]([O-])=O)C=C([N+]([O-])=O)C=1)[N+]([O-])=O>C(#N)C>[CH2:1]([N:15]1[CH:16]=[CH:17][N:18]=[C:14]1[C:12]([C:9]1[CH:8]=[CH:7][C:6]([Cl:5])=[CH:11][CH:10]=1)([C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)[OH:13])[CH:2]=[CH2:3]

Participants

6

Reactant 4

HCID 6954Picric AcidHCID 7841Allyl bromideHCID 14798Sodium HydroxideHCID 12433863(4-chlorophenyl)(1H-imidazol-2-yl)phenylmethanol

Product 1

HCID 124339291-Allyl-alpha-(p-chlorophenyl)-alpha-phenylimidazole-2-methanol

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of 3.4 g (0.028 mol) of freshly distilled allyl bromide, 7 g (0.025 mol) of α-(p-chlorophenyl)-α-phenylimidazole-2-methanol (prepared according to Example IV), 1.2 g (0.030 mol) of sodium hydroxide, 0.050 g of picric acid and 50 ml. of acetonitrile was refluxed for 5 hours. The warm reaction mixture was filtered and water was added to the filtrate. The precipitate formed was filtered off, washed with water and petroleum ether (boiling range 40°-60° C.) and three times crystallised from isopropyl alcohol. 1-Allyl-α-(p-chlorophenyl)-α-phenylimidazole-2-methanol was obtained. Melting point 165°-165.5° C.

Workup

  1. customThe warm reaction mixture
  2. filtrationwas filtered
  3. additionwater was added to the filtrate
  4. customThe precipitate formed
  5. filtrationwas filtered off
  6. washwashed with water and petroleum ether (boiling range 40°-60° C.) and three times
  7. customcrystallised from isopropyl alcohol

Sources & evidence

ORD record
ord-9019765763da459a8ba96ec7d4673355
Source dataset
uspto-grants-1979_05
Patent number
US04152441

Linked notes

Loading…