Thionyl Chloride → HCID 19010314, compound

HRID 1741612Notes

Reaction equation

HRID 1741612 reaction equation
O[CH2:2][C:3]1[CH:12]=[CH:11][C:6]([C:7]([O:9][CH3:10])=[O:8])=[C:5]([C:13]2[NH:14][C:15](=[O:22])[C:16]([CH:19]([CH3:21])[CH3:20])([CH3:18])[N:17]=2)[N:4]=1.S(Cl)([Cl:25])=O>C(Cl)(Cl)Cl>[Cl:25][CH2:2][C:3]1[CH:12]=[CH:11][C:6]([C:7]([O:9][CH3:10])=[O:8])=[C:5]([C:13]2[NH:14][C:15](=[O:22])[C:16]([CH:19]([CH3:21])[CH3:20])([CH3:18])[N:17]=2)[N:4]=1

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 19010306HCID 19010306, compound

Product 1

HCID 19010314HCID 19010314, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

To a solution of 8.7 g of methyl 6-hydroxymethyl-2-(4-isopropyl-4-methyl-5-oxo-2-imidazolin-2-yl)nicotinate in 90 mL chloroform, stirred at room temperature, is added dropwise 4.2 mL of thionyl chloride. When the addition is complete, the solution is heated at reflux for 1 hour. The reaction is concentrated in vacuo, and the residue is dissolved in methylene chloride and washed with saturated sodium bicarbonate solution. The organic phase is dried and concentrated in vacuo to an oil. Trituration of this oil affords the desired product as a solid. Recrystallization from methylene chloride-hexane gives analytically pure material, mp 127°-129° C.

Workup

  1. additionWhen the addition
  2. temperaturethe solution is heated
  3. temperatureat reflux for 1 hour
  4. concentrationThe reaction is concentrated in vacuo
  5. dissolutionthe residue is dissolved in methylene chloride
  6. washwashed with saturated sodium bicarbonate solution
  7. customThe organic phase is dried
  8. concentrationconcentrated in vacuo to an oil

Sources & evidence

ORD record
ord-afefd9e8d7b64b4f82e23adf03492c48
Source dataset
uspto-grants-1994_08
Patent number
US05334576

Reaction notes

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