Hydrochloric Acid → HCID 69947512, compound

HRID 1416051Notes

Reaction equation

HRID 1416051 reaction equation
[Cl:1][CH2:2][C:3]1[CH:7]=[CH:6][S:5][CH:4]=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>CN(C)C=O.O.C(O)C>[ClH:1].[Cl:17][C:15]1[CH:14]=[C:13]([S:18][C:19]2[N:23]([CH2:2][C:3]3[CH:7]=[CH:6][S:5][CH:4]=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 124874623-(Chloromethyl)thiopheneHCID 178491401HCID 178491401, compound

Product 1

HCID 69947512HCID 69947512, compoundYield 97%

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

In dimethylformamide was added 67 mg of 3-(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, and the solvent was distilled off under reduced pressure. To thus-obtained oil was 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 200 mg of Compound I-127 was obtained (yield 97%).

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. washThe crystals were washed with diethyl ether
  13. filtrationfiltered
  14. customwas obtained (yield 97%)

Sources & evidence

ORD record
ord-5829e3941b7d4037bdda0a138adcae3d
Source dataset
uspto-grants-1999_06
Patent number
US05910506

Reaction notes

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