Acetic Acid → HCID 15508343, compound

HRID 1419508Notes

Reaction equation

HRID 1419508 reaction equation
CS(O)(=O)=O.[C:6]([OH:9])(=O)[CH3:7].[NH:10]1[CH2:15][CH2:14][NH:13][CH:12]=[C:11]1[C:16]#[N:17].[CH3:18][CH:19]([CH3:21])[CH3:20].[OH-:22].[Na+]>>[C:19]([NH:17][C:16]([C:11]1[N:10]([C:6](=[O:9])[CH3:7])[CH2:15][CH2:14][NH:13][CH:12]=1)=[O:22])([CH3:21])([CH3:20])[CH3:18]

Participants

6

Reactant 5

HCID 176Acetic AcidHCID 6360IsobutaneHCID 6395Methanesulfonic AcidHCID 14798Sodium HydroxideHCID 117891511,4,5,6-Tetrahydro-2-pyrazinecarbonitrile

Product 1

HCID 15508343HCID 15508343, compound

Conditions

Temperature
20 °C

Procedure

70 g (0.77 mmol) of methanesulfonic acid was added slowly to 100 ml (1.75 mol) of acetic acid at room temperature, followed by 20.0 g (184 mmol) of 1,4,5,6-tetrahydropyrazine-2-carbonitrile. 23.0 g (410 mmol) of isobutane were introduced into this mixture at 25° C. and the resulting mixture was stirred for 5 hours. This was then neutralized with 30% sodium hydroxide solution, the temperature always being kept below 30° C. The mixture was adjusted to pH 8-10 and extracted with three times 200 ml of methyl ethyl ketone. The combined organic phases were dried over magnesium sulfate and the solvent was distilled off. The residue (41.2 g) was dissolved in 80 ml of ethyl acetate, with heating. After cooling to 20° C., 500 ml of hexane was added, the mixture was cooled further to 0° C. and, after 1 hour, the precipitated product was filtered off and dried. The yield was 32.6 g (79%) of light beige powder. The melting point of the title compound was: 151.3° to 152.6° C. Other data concerning the product was:

Workup

  1. customalways being kept below 30° C
  2. extractionextracted with three times 200 ml of methyl ethyl ketone
  3. dry with materialThe combined organic phases were dried over magnesium sulfate
  4. distillationthe solvent was distilled off
  5. dissolutionThe residue (41.2 g) was dissolved in 80 ml of ethyl acetate
  6. temperaturewith heating
  7. addition500 ml of hexane was added
  8. temperaturethe mixture was cooled further to 0° C. and, after 1 hour
  9. filtrationthe precipitated product was filtered off
  10. customdried
  11. custom151.3° to 152.6° C

Sources & evidence

ORD record
ord-909fdd3c588c4e3281a29750c6ca8b9c
Source dataset
uspto-grants-1999_03
Patent number
US05886181

Reaction notes

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