Methanol → HCID 178498852, compound

HRID 340087Notes

Reaction equation

HRID 340087 reaction equation
S(Cl)(Cl)=O.[OH:5][C:6]1[N:7]=[CH:8][C:9]([C:12]([OH:14])=[O:13])=[N:10][CH:11]=1.[CH3:15]O>>[CH3:15][O:13][C:12]([C:9]1[CH:8]=[N:7][C:6]([OH:5])=[CH:11][N:10]=1)=[O:14]

Participants

4

Reactant 3

HCID 887MethanolHCID 24386Thionyl ChlorideHCID 1785247745-Hydroxypyrazine-2-carboxylic acid

Product 1

HCID 178498852HCID 178498852, compoundYield 65%

Procedure

Thionyl chloride (152 mL, 2.08 mol) was added dropwise at 20° C. to methanol (5 L). After the addition was completed, the mixture was stirred at this temperature for 30 minutes. Then 5-hydroxy-pyrazine-2-carboxylic acid (100 g, 714 mmol) was added, and the mixture was heated at reflux for 2 hours. The reaction mixture was concentrated in vacuo, and the residue was recrystallised from methanol (400 mL) to give 71 g (464 mmol) of the title compound in 65% yield.

Workup

  1. additionAfter the addition
  2. temperaturethe mixture was heated
  3. temperatureat reflux for 2 hours
  4. concentrationThe reaction mixture was concentrated in vacuo
  5. customthe residue was recrystallised from methanol (400 mL)

Sources & evidence

ORD record
ord-a6ade49149ac40c3a7e9d1cadf144c3a
Source dataset
uspto-grants-2014_11
Patent number
US08895544B2

Reaction notes

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