Benzyl Chloride → HCID 14129244, compound

HRID 1762036Notes

Reaction equation

HRID 1762036 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[N:7]1[CH:11]=[CH:10][N:9]=[C:8]1[SH:12].C(=O)([O-])[O-].[K+].[K+].[CH2:19](Cl)[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1>C(#N)C>[CH2:19]([S:12][C:8]1[N:7]([C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][N:1]=2)[CH:11]=[CH:10][N:9]=1)[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1

Participants

5

Reactant 3

HCID 7503Benzyl ChlorideHCID 11430Potassium CarbonateHCID 178527868HCID 178527868, compound

Product 1

HCID 14129244HCID 14129244, compoundYield 92.3%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture consisting of 5.1 g of 1-(2-pyridyl)imidazole-2-thiol, 5.2 g of anhydrous potassium carbonate, 3.7 g of benzyl chloride and 50 ml of acetonitrile was stirred at room temperature for 4 hours. After completion of the reaction, solids were filtered off and the filtrate was concentrated under reduced pressure. Crystals precipitated were collected by filtration to give 7.1 g of 2-benzylthio-1-(2-pyridyl)imidazole (m.p.: 76° to 77° C.). To a mixture consisting of 7.1 g of the thus obtained crystals, 50 ml of methylene chloride, 50 ml of water and 22 g of conc. hydrochloric acid was added dropwise 80 g of 6% sodium hypochlorite solution under vigorous stirring at -10° to 0° C. over 1 hour. After completion of the dropwise addition, the resulting mixture was stirred at the same temperature for 30 minutes. Then, the organic layer was separated and the aqueous layer was extracted with methylene chloride. After the organic layers were combined and washed with water, to the organic layer was added dropwise 10 ml of a 28% aqueous ammonia under ice-cooling while vigorous stirring. After completion of the dropwise addition, the resulting mixture was stirred at room temperature for 1.5 hours. The reaction mixture was concentrated to dryness and the thus obtained concentrated residue was extracted with ethyl acetate. The organic layer was concentrated under reduced pressure to give 3.0 g of a crude product of the desired compound. Crystals precipitated from the resulting crude product were collected by filtration to give 0.8 g of the desired compound. m.p.: 187° to 188° C.

Workup

  1. customAfter completion of the reaction, solids
  2. filtrationwere filtered off
  3. concentrationthe filtrate was concentrated under reduced pressure
  4. customCrystals precipitated
  5. filtrationwere collected by filtration

Sources & evidence

ORD record
ord-90f0509c708347cf83df8606fb7bf4db
Source dataset
uspto-grants-1989_05
Patent number
US04830660

Reaction notes

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