Dimethylformamide → 5-Chloropyrazinoic acid

HRID 655777Notes

Reaction equation

HRID 655777 reaction equation
O[C:2]1[N:3]=[CH:4][C:5]([C:8]([OH:10])=[O:9])=[N:6][CH:7]=1.CN(C)C=O.S(Cl)([Cl:18])=O>>[Cl:18][C:2]1[N:3]=[CH:4][C:5]([C:8]([OH:10])=[O:9])=[N:6][CH:7]=1

Participants

4

Reactant 3

HCID 6228DimethylformamideHCID 24386Thionyl ChlorideHCID 1785247745-Hydroxypyrazine-2-carboxylic acid

Product 1

HCID 4654725-Chloropyrazinoic acidYield 75%

Procedure

5-Hydroxypyrazine-2-carboxylic acid (1.0 g, 0.007 mol) was taken in thionyl chloride (10 mL), to this solution dimethylformamide (0.1 mL) was added which was heated to reflux for 16 h. After this period, excess thionyl chloride was distilled off to get crude compound, which was added to ice (20 g) and extracted with ethyl acetate (2×70 mL). The organic layers were combined and dried over anhydrous sodium sulphate and concentrated under reduced pressure to obtain brown solid which was triturated with diethyl ether (30 mL) to afford 600 mg (75%) of 5-chloropyrazine-2-carboxylic acid.

Workup

  1. additionwas added which
  2. temperaturewas heated
  3. temperatureto reflux for 16 h
  4. waitAfter this period
  5. distillationexcess thionyl chloride was distilled off
  6. customto get crude compound, which
  7. extractionextracted with ethyl acetate (2×70 mL)
  8. dry with materialdried over anhydrous sodium sulphate
  9. concentrationconcentrated under reduced pressure
  10. customto obtain brown solid which
  11. customwas triturated with diethyl ether (30 mL)

Sources & evidence

ORD record
ord-7c734bbda8984c5ca7e6c413be1df7f6
Source dataset
uspto-grants-2011_12
Patent number
US08071605B2

Reaction notes

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