Potassium Iodide → 1-[(Benzyloxy)methyl]-alpha,alpha-bis(p-chlorophenyl)imidazole-2-methanol

HRID 261973

Reaction equation

HRID 261973 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([C:15]2[CH:20]=[CH:19][C:18]([Cl:21])=[CH:17][CH:16]=2)([C:10]2[NH:11][CH:12]=[CH:13][N:14]=2)[OH:9])=[CH:4][CH:3]=1.[OH-].[Na+].C1(C(O)=C([N+]([O-])=O)C=C([N+]([O-])=O)C=1)[N+]([O-])=O.[I-].[K+].[CH2:42]([O:49][CH2:50]Cl)[C:43]1[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=1>C(#N)C>[CH2:42]([O:49][CH2:50][N:14]1[CH:13]=[CH:12][N:11]=[C:10]1[C:8]([C:15]1[CH:20]=[CH:19][C:18]([Cl:21])=[CH:17][CH:16]=1)([C:5]1[CH:4]=[CH:3][C:2]([Cl:1])=[CH:7][CH:6]=1)[OH:9])[C:43]1[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=1

Participants

7

Reactant 5

HCID 4875Potassium IodideHCID 6954Picric AcidHCID 14798Sodium HydroxideHCID 137983Benzyl chloromethyl etherHCID 12433870Bis-(4-chloro-phenyl)-(1H-imidazol-2-yl)-methanol

Product 1

HCID 34440691-[(Benzyloxy)methyl]-alpha,alpha-bis(p-chlorophenyl)imidazole-2-methanol

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent2×

Conditions

Temperature
50 °C

Procedure

A mixture of 125 ml. of acetonitrile, 9.2 g of α,α-bis(p-chlorophenyl)imidazole-2-methanol (prepared according to Example III) and 1.5 g of sodium hydroxide was stirred for one hour. To the--now homogeneous--reaction mixture 500 mg of picric acid and a few crystals of potassium iodide were added and the mixture was heated to 50° C. A solution of 5.2 g of benzyloxymethyl chloride in 50 ml. of acetonitrile was then added dropwise and the reaction mixture was subsequently refluxed for 4 hours. The mixture was cooled and filtered and the filtrate was concentrated under reduced pressure. The residue was suspended in water and the suspension was extracted with diethyl ether. The extract was dried over sodium sulphate and the ether was distilled off. The solid residue obtained was crystallized from isopropyl alcohol. The product was then boiled four times with 75 ml. of petroleum ether (boiling range 60°-80° C.), the petroleum ether being decanted each time, after which it was once again crystallized from isopropyl alcohol. The substance was dried in vacuo for 10 hours at 110° C. 1-[(Benzyloxy)methyl]-α,α-bis(p-chlorophenyl)imidazole-2-methanol was obtained. Melting point 139°-141° C.

Workup

  1. additionA mixture of 125 ml
  2. temperaturethe reaction mixture was subsequently refluxed for 4 hours
  3. temperatureThe mixture was cooled
  4. filtrationfiltered
  5. concentrationthe filtrate was concentrated under reduced pressure
  6. extractionthe suspension was extracted with diethyl ether
  7. dry with materialThe extract was dried over sodium sulphate
  8. distillationthe ether was distilled off
  9. customThe solid residue obtained
  10. customwas crystallized from isopropyl alcohol
  11. customof petroleum ether (boiling range 60°-80° C.), the petroleum ether being decanted each time
  12. customafter which it was once again crystallized from isopropyl alcohol
  13. customThe substance was dried in vacuo for 10 hours at 110° C

Sources & evidence

ORD record
ord-dfc1f11540a14a0b9581d3579560ae13
Source dataset
uspto-grants-1979_05
Patent number
US04152441

Linked notes

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