Hydrochloric Acid → 1H-Imidazole-2-methanol, 5-((3,5-dichlorophenyl)thio)-4-(1-methylethyl)-1-((2-nitrophenyl)methyl)-

HRID 1857742Notes

Reaction equation

HRID 1857742 reaction equation
[N+:1]([C:4]1[CH:11]=[CH:10][CH:9]=[CH:8][C:5]=1[CH2:6]Cl)([O-:3])=[O:2].[I-].[K+].[Cl:14][C:15]1[CH:16]=[C:17]([S:22][C:23]2[NH:27][C:26]([CH2:28][O:29]CC3C=CC(OC)=CC=3)=[N:25][C:24]=2[CH:39]([CH3:41])[CH3:40])[CH:18]=[C:19]([Cl:21])[CH:20]=1.C(=O)([O-])[O-].[K+].[K+].Cl>O.C(O)C.CN(C)C=O>[Cl:21][C:19]1[CH:18]=[C:17]([S:22][C:23]2[N:27]([CH2:6][C:5]3[CH:8]=[CH:9][CH:10]=[CH:11][C:4]=3[N+:1]([O-:3])=[O:2])[C:26]([CH2:28][OH:29])=[N:25][C:24]=2[CH:39]([CH3:41])[CH3:40])[CH:16]=[C:15]([Cl:14])[CH:20]=1

Participants

9

Reactant 5

HCID 313Hydrochloric AcidHCID 4875Potassium IodideHCID 11430Potassium CarbonateHCID 119212-Nitrobenzyl chlorideHCID 178491401HCID 178491401, compound

Product 1

HCID 4740341H-Imidazole-2-methanol, 5-((3,5-dichlorophenyl)thio)-4-(1-methylethyl)-1-((2-nitrophenyl)methyl)-Yield 47.1%

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To dimethylformamide was added 237 mg of o-nitrobenzyl chloride and 228 mg of potassium iodide under ice-cooling, the mixture was allowed to warm up to room temperature and stirred for 20 minutes. Then, 400 mg of 5-(3,5-dichlorophenylthio)-4-isopropyl-2-(p-methoxybenzyloxymethyl)-1H-imidazole (101b) was added, followed by addition of 152 mg of potassium carbonate. Then, the mixture was warmed up to 50° C., and allowed to react for 6 hours. After completion of the reaction, the mixture was diluted with water, extracted with diethyl ether, the extract was dried over sodium sulfate, and the solvent was distilled off under reduced pressure. To thus-obtained oil were added 10 ml of ethanol and 20 ml of 36% hydrochloric acid, and the mixture was stirred at 90° C. for 2 hours. After completion of the reaction, the solvent was distilled off under reduced pressure, an aqueous sodium hydrogen carbonate solution was added, extracted with ethyl acetate, the extract was dried over sodium sulfate, and the solvent was distilled off under reduced pressure. The crystals were washed with diethyl ether, filtered, and 195 mg of 5-(3,5-dichlorophenylthio)-2-hydroxymethyl-4-isopropyl-1-(o-nitrobenzyl)-1H-imidazole (103c) was obtained (yield 47%). mp 160-166° C.

Workup

  1. temperaturecooling
  2. temperatureThen, the mixture was warmed up to 50° C.
  3. customto react for 6 hours
  4. customAfter completion of the reaction
  5. extractionextracted with diethyl ether
  6. dry with materialthe extract was dried over sodium sulfate
  7. distillationthe solvent was distilled off under reduced pressure
  8. customTo thus-obtained oil
  9. stirringthe mixture was stirred at 90° C. for 2 hours
  10. customAfter completion of the reaction
  11. distillationthe solvent was distilled off under reduced pressure
  12. additionan aqueous sodium hydrogen carbonate solution was added
  13. extractionextracted with ethyl acetate
  14. dry with materialthe extract was dried over sodium sulfate
  15. distillationthe solvent was distilled off under reduced pressure
  16. washThe crystals were washed with diethyl ether
  17. filtrationfiltered

Sources & evidence

ORD record
ord-09f04a4a2f2246b880c961467dee9a15
Source dataset
uspto-grants-2000_11
Patent number
US06147097

Reaction notes

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