Water → HCID 22923792, compound

HRID 2258314Notes

Reaction equation

HRID 2258314 reaction equation
Cl[C:2]1[C:3]([C:18]([O:20]CC2C=CC=CC=2)=[O:19])=[N:4][CH:5]=[C:6]([C:8]([O:10]CC2C=CC=CC=2)=[O:9])[CH:7]=1.[CH3:28][S-:29].[Na+].O>CS(C)=O>[CH3:28][S:29][C:2]1[C:3]([C:18]([OH:20])=[O:19])=[N:4][CH:5]=[C:6]([C:8]([OH:10])=[O:9])[CH:7]=1

Participants

5

Reactant 3

HCID 962WaterHCID 4378561Sodium methanethiolateHCID 22923807HCID 22923807, compound

Product 1

HCID 22923792HCID 22923792, compoundYield 109.4%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
140 °C

Procedure

4.6 g (12 mmol) of dibenzyl 3-chloropyridine-2,5-dicarboxylate were dissolved, at 20° C. and while stirring, in 30 ml of dimethyl sulfoxide, and after that 5.0 g (70 mmol) of sodium thiomethoxide were added, in association with which the temperature rose to 80° C. The reaction mixture was heated at 140° C. for 1 h and then cooled down, after which water was added to it; the oily layer was separated off and cone. hydrochloric acid (pH 1) was added to the aqueous DMSO phase, and the precipitated product was filtered off with suction. 2.8 g of yellow crystalline product were obtained, m.p. 223° C. (with decomposition).

Workup

  1. customrose to 80° C
  2. temperaturecooled down
  3. customthe oily layer was separated off
  4. additionhydrochloric acid (pH 1) was added to the aqueous DMSO phase
  5. filtrationthe precipitated product was filtered off with suction

Sources & evidence

ORD record
ord-67214511b1da4b538ad9996242adb5aa
Source dataset
uspto-grants-1997_08
Patent number
US05658933

Reaction notes

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