Hydrochloric Acid → HCID 22130574, compound

HRID 1857745Notes

Reaction equation

HRID 1857745 reaction equation
[Cl:1][CH2:2][C:3]1[S:4][CH:5]=[CH:6][CH:7]=1.[I-].[K+].[Cl:10][C:11]1[CH:12]=[C:13]([S:18][C:19]2[NH:23][C:22]([CH2:24][O:25]CC3C=CC(OC)=CC=3)=[N:21][C:20]=2[CH:35]([CH3:37])[CH3:36])[CH:14]=[C:15]([Cl:17])[CH:16]=1.C(=O)([O-])[O-].[K+].[K+].Cl>O.C(O)C.CN(C)C=O>[ClH:1].[Cl:17][C:15]1[CH:14]=[C:13]([S:18][C:19]2[N:23]([CH2:2][C:3]3[S:4][CH:5]=[CH:6][CH:7]=3)[C:22]([CH2:24][OH:25])=[N:21][C:20]=2[CH:35]([CH3:37])[CH3:36])[CH:12]=[C:11]([Cl:10])[CH:16]=1

Participants

9

Reactant 5

HCID 313Hydrochloric AcidHCID 4875Potassium IodideHCID 11430Potassium CarbonateHCID 698302-(Chloromethyl)thiopheneHCID 178491401HCID 178491401, compound

Product 1

HCID 22130574HCID 22130574, compoundYield 83%

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To dimethylformamide was added 67 mg of 2-(chloromethyl)thiophene and 152 mg of potassium iodide under ice-cooling, the mixture was allowed to warm up to room temperature and stirred for 20 minutes. Then, 200 mg of 5-(3,5-dichlorophenylthio)-4-isopropyl-2-(p-methoxybenzyloxymethyl)-1H-imidazole (101b) was added, followed by addition of 126 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, arid the solvent was distilled off under reduced pressure. To thus-obtained oil were added 5 ml of ethanol and 10 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. The crystals were washed with diethyl ether, filtered, and 170 mg of Compound I-126 was obtained (yield 83%).

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. distillationwas 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. washThe crystals were washed with diethyl ether
  13. filtrationfiltered

Sources & evidence

ORD record
ord-3e5c46a3d382449c8e36c99419c6f003
Source dataset
uspto-grants-2000_11
Patent number
US06147097

Reaction notes

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