Hydrochloric Acid → HCID 20497993, compound

HRID 2166834Notes

Reaction equation

HRID 2166834 reaction equation
C[O-].[Na+].[CH2:4]([SH:7])[CH:5]=[CH2:6].Cl.Cl[CH:10]([N:20]1[CH:24]=[CH:23][N:22]=[CH:21]1)[CH2:11][C:12]1[CH:17]=[CH:16][C:15]([Cl:18])=[CH:14][C:13]=1[Cl:19].Cl>CO.CC(C)=O.C(O)(C)C.CCOCC.O>[CH2:4]([S:7][CH:10]([N:20]1[CH:24]=[CH:23][N:22]=[CH:21]1)[CH2:11][C:12]1[CH:17]=[CH:16][C:15]([Cl:18])=[CH:14][C:13]=1[Cl:19])[CH:5]=[CH2:6]

Participants

10

Reactant 4

HCID 313Hydrochloric AcidHCID 13367Allyl MercaptanHCID 10942334Sodium MethoxideHCID 70531060HCID 70531060, compound

Product 1

HCID 20497993HCID 20497993, compound

Reagents, catalysts & solvents 5

HCID 180AcetoneSolventHCID 887MethanolSolvent2×HCID 962WaterSolventHCID 3283Diethyl EtherSolventHCID 3776IsopropanolSolvent

Procedure

To a solution of 1.08 g (0.02 mole) of sodium methoxide in 50 ml of methanol was added 1.48 g (0.02 mole) of allyl mercaptan. To this solution was added a solution of 3.12 g (0.01 mole) of 1-(α-chloro-2,4-dichlorophenethyl) imidazole hydrochloride as prepared in Examples 1A to 1C, in 50 ml of methanol. The mixture was heated at reflux for 5 hours, cooled, and poured into 400 ml of H2O. The organic phase was extracted with ether, the combined ether extracts washed with H2O, and dried over MgSO4. Evaporation gave a dark brown oil. The oil was dissolved in a minimum of acetone and treated with an excess of HCl in isopropyl alcohol. Addition of ether caused a gummy solid to separate. Trituration of the gum with ether converted it to a solid that was recrystallized from ethanol-ether with a charcoal treatment. The product, 0.6 g (19%), was a white crystalline solid, m.p. 97°-102° C.

Workup

  1. temperatureThe mixture was heated
  2. temperatureat reflux for 5 hours
  3. temperaturecooled
  4. extractionThe organic phase was extracted with ether
  5. washthe combined ether extracts washed with H2O
  6. dry with materialdried over MgSO4
  7. customEvaporation
  8. customgave a dark brown oil
  9. customto separate
  10. customthat was recrystallized from ethanol-ether with a charcoal treatment

Sources & evidence

ORD record
ord-dc5f88690f994713ad597c668b9a866b
Source dataset
uspto-grants-1983_06
Patent number
US04389409

Reaction notes

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