Acetic Acid → HCID 178510038, compound

HRID 243535Notes

Reaction equation

HRID 243535 reaction equation
C(O)CCC.CC(C)([O-])C.[K+].CCOC([CH:17]([C:20]1([C:25]#[N:26])[CH2:24][CH2:23][CH2:22][CH2:21]1)C#N)=O.[C:27]([N:29](C1C=CC=CC=1)[C:30]([NH2:32])=[NH:31])#[N:28].[C:39]([OH:42])(=O)[CH3:40]>O>[NH2:28][C:27]1[CH:40]=[C:39]([OH:42])[N:31]=[C:30]([NH:32][C:22]2[CH:21]=[CH:17][C:20]([C:25]#[N:26])=[CH:24][CH:23]=2)[N:29]=1

Participants

7

Reactant 5

HCID 176Acetic AcidHCID 2631-Butanol3×HCID 16226777Ethyl 2-cyano-2-(1-cyanocyclopentyl)acetateHCID 23665647Potassium tert-butoxideHCID 53954996Phenylcyanoguanidine

Product 1

HCID 178510038HCID 178510038, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
60 °C

Procedure

2000 ml of n-butanol and 192.8 g of potassium-tert-butoxide were added to the reaction vessel at 45±5° C. and stirred for 30 mins. To the reaction mixture was added 194.42 g of ethylcyano acetate over 15 min and added 250 ml of n-butanol. The reaction mixture was heated to 60±5° C. under stirring and 250 g of N-cyanophenyl guanidine was added, followed by 250 ml of n-butanol and further heated to 93±3° C., maintained the same at 4 hrs with stirring. After completion of the reaction, the reaction mixture was cooled to 75±5° C. and 1750 ml of water was added and stirred at the same temperature for 30 mins. Further to the reaction mass was added 250 ml of glacial acetic acid; stirred and cooled to room temperature (RT). The resulting solid was filtered and washed with 500 ml of water, followed by washing with methanol and drying to yield the titled compound.

Workup

  1. stirringunder stirring
  2. temperaturefurther heated to 93±3° C.
  3. temperaturemaintained the same at 4 hrs
  4. stirringwith stirring
  5. customAfter completion of the reaction
  6. temperaturethe reaction mixture was cooled to 75±5° C.
  7. stirringstirred at the same temperature for 30 mins
  8. stirringstirred
  9. temperaturecooled to room temperature (RT)
  10. filtrationThe resulting solid was filtered
  11. washwashed with 500 ml of water
  12. washby washing with methanol
  13. customdrying

Sources & evidence

ORD record
ord-81e4b4559dbc43efa57fb86a25cc0d0f
Source dataset
uspto-grants-2014_02
Patent number
US08653266B2

Reaction notes

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