Thioglycolic Acid → HCID 13336850, compound

HRID 1462288Notes

Reaction equation

HRID 1462288 reaction equation
[C:1]([OH:5])(=[O:4])[CH2:2][SH:3].[C:6]([C:8]1[C:13]([C:14]#[N:15])=[N:12][C:11](Cl)=[CH:10][N:9]=1)#[N:7].C(N(CC)CC)C>CC(C)=O>[C:6]([C:8]1[C:13]([C:14]#[N:15])=[N:12][C:11]([S:3][CH2:2][C:1]([OH:5])=[O:4])=[CH:10][N:9]=1)#[N:7]

Participants

5

Reactant 3

HCID 1133Thioglycolic AcidHCID 8471TriethylamineHCID 129071975-Chloropyrazine-2,3-dicarbonitrile

Product 1

HCID 13336850HCID 13336850, compoundYield 75%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

Thioglycolic acid (0.92 g; 0.01 mole) and 1.64 g (0.01 mole) of 2,3-dicyano-5-chloropyrazine were dissolved in 40 ml of acetone, and while the solution was cooled to 0° to 5° C., 2.12 g (0.021 mole) of triethylamine was added dropwise. After the addition, the mixture was stirred at 20° to 25° C. for 2 hours. The precipitate was separated by filtration. The filtrate was concentrated under reduced pressure, and 100 ml of a 1% aqueous solution of hydrochloric acid was added. The separated oily product was extracted with 50 ml of ethyl acetate. The ethyl acetate layer was washed twice with 50 ml of a saturated aqueous solution of sodium chloride, dried over anhydrous sodium sulfate, and concentrated under reduced pressure to afford a crude product. Recrystallization from toluene afforded 1.65 g (yield 75%) of 2,3-dicyano-5-(carboxymethylthio)pyrazine.

Workup

  1. temperaturewhile the solution was cooled to 0° to 5° C.
  2. additionAfter the addition
  3. customThe precipitate was separated by filtration
  4. concentrationThe filtrate was concentrated under reduced pressure, and 100 ml of a 1% aqueous solution of hydrochloric acid
  5. additionwas added
  6. extractionThe separated oily product was extracted with 50 ml of ethyl acetate
  7. washThe ethyl acetate layer was washed twice with 50 ml of a saturated aqueous solution of sodium chloride
  8. dry with materialdried over anhydrous sodium sulfate
  9. concentrationconcentrated under reduced pressure
  10. customto afford a crude product
  11. customRecrystallization from toluene

Sources & evidence

ORD record
ord-34392308b4734f7bbe1f7d7aa3aec007
Source dataset
uspto-grants-1984_07
Patent number
US04460403

Reaction notes

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