Methanol → HCID 13960810, compound

HRID 2308813Notes

Reaction equation

HRID 2308813 reaction equation
[CH3:1][NH:2][C:3]([C:5]1[CH:10]=[C:9]([C:11]([OH:13])=[O:12])[CH:8]=[C:7]([C:14](=[O:17])[NH:15][CH3:16])[N:6]=1)=[O:4].S(Cl)(Cl)=O.[CH3:22]O>>[CH3:1][NH:2][C:3]([C:5]1[CH:10]=[C:9]([C:11]([O:13][CH3:22])=[O:12])[CH:8]=[C:7]([C:14](=[O:17])[NH:15][CH3:16])[N:6]=1)=[O:4]

Participants

4

Reactant 3

HCID 887MethanolHCID 24386Thionyl Chloride2×HCID 13960809HCID 13960809, compound

Product 1

HCID 13960810HCID 13960810, compound

Procedure

2,6-Bis(N-methylcarbamoyl)pyridine-4-carboxylic acid (1 g) was mixed with methanol (50 ml), and to the mixture was added thionyl chloride (2 ml). After addition of thionyl chloride, the mixture was stirred at room temperature overnight. The mixture was then evaporated under reduced pressure, and water was added to the residue followed by extraction with chloroform. The organic layer was washed with a saturated sodium bicarbonate aqueous solution, and evaporated to dryness. The residual crystals were recrystallized from toluene to give 0.4 g of methyl 2,6-bis(N-methylcarbamoyl)pyridine-4-carboxylate. m.p. 202°-203° C.

Workup

  1. customThe mixture was then evaporated under reduced pressure, and water
  2. additionwas added to the residue
  3. extractionfollowed by extraction with chloroform
  4. washThe organic layer was washed with a saturated sodium bicarbonate aqueous solution
  5. customevaporated to dryness
  6. customThe residual crystals were recrystallized from toluene

Sources & evidence

ORD record
ord-c68930ef22b041e1a81ce2a80e6fa7e1
Source dataset
uspto-grants-1987_09
Patent number
US04691018

Reaction notes

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