Thionyl Chloride → HCID 18960790, compound

HRID 1084342Notes

Reaction equation

HRID 1084342 reaction equation
O[CH2:2][CH2:3][CH2:4][C:5]1[C:6]([C:15]([O:17][CH3:18])=[O:16])=[CH:7][C:8]([C:11]([O:13][CH3:14])=[O:12])=[N:9][CH:10]=1.S(Cl)([Cl:21])=O>C(Cl)(Cl)Cl>[Cl:21][CH2:2][CH2:3][CH2:4][C:5]1[C:6]([C:15]([O:17][CH3:18])=[O:16])=[CH:7][C:8]([C:11]([O:13][CH3:14])=[O:12])=[N:9][CH:10]=1

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 18960797HCID 18960797, compound

Product 1

HCID 18960790HCID 18960790, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Conditions

Temperature
0 °C

Procedure

370 mg of dimethyl 5-(3- hydroxypropyl)-pyridine-2,4-dicarboxylate (from Example 16) are dissolved in 10 ml of chloroform, the solution is cooled to 0° C. and 0.18 ml of thionyl chloride in 2 ml of chloroform are slowly added. The mixture is subsequently stirred at room temperature for one hour and then at 60° C. for one hour. After cooling, the mixture is evaporated and the residue is taken up in chloroform and water; the phases are separated and the organic phase is washed with sodium sulfate solution, dried over magnesium sulfate and evaporated. After chromatography on silica gel, 286 mg of a yellow oil remain.

Workup

  1. waitat 60° C. for one hour
  2. temperatureAfter cooling
  3. customthe mixture is evaporated
  4. customthe phases are separated
  5. washthe organic phase is washed with sodium sulfate solution
  6. dry with materialdried over magnesium sulfate
  7. customevaporated

Sources & evidence

ORD record
ord-ea06375bb0204274a9d85083526149e1
Source dataset
uspto-grants-1991_04
Patent number
US05004748

Reaction notes

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