Hydrochloric Acid → HCID 178418396, compound

HRID 1377635Notes

Reaction equation

HRID 1377635 reaction equation
C(OC([NH:8][C:9]1[CH:14]=[CH:13][C:12]([CH:15]([C:18](=O)[CH3:19])[C:16]#[N:17])=[CH:11][CH:10]=1)=O)(C)(C)C.C(O)C.C(O[CH:27](OCC)[CH2:28][NH:29][NH2:30])C.[ClH:34]>O1CCOCC1.C(OCC)(=O)C>[ClH:34].[NH2:8][C:9]1[CH:10]=[CH:11][C:12]([C:15]2[C:18]([CH3:19])=[N:30][N:29]3[CH:28]=[CH:27][NH:17][C:16]=23)=[CH:13][CH:14]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 702EthanolHCID 322952(2,2-Diethoxyethyl)hydrazineHCID 196943922-(4-t-Butoxycarbonylaminophenyl)-3-oxobutyronitrile

Product 1

HCID 178418396HCID 178418396, compound

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolventHCID 312751,4-DioxaneSolvent

Procedure

A mixture of 2.5 g of 2-(4-t-butoxycarbonylamino-phenyl)-3-oxobutyronitrile, 20 ml of ethanol and 1.4 g of 2,2-diethoxyethylhydrazine was heated under reflux for 2 hours. 20 ml of 4N hydrogen chloride in dioxane were added, and then the whole mixture was heated under reflux for a further 30 minutes. After the mixture had been cooled, ethyl acetate was added to precipitate crystals. These crystals were collected by filtration and recrystallized from ethanol to give 1.4 g of the title compound as pale brown plates melting at 180°-190° C.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 2 hours
  3. temperaturethe whole mixture was heated
  4. temperatureunder reflux for a further 30 minutes
  5. temperatureAfter the mixture had been cooled
  6. customto precipitate crystals
  7. filtrationThese crystals were collected by filtration
  8. customrecrystallized from ethanol

Sources & evidence

ORD record
ord-02cfdc9463174e62811e94a52ad3682d
Source dataset
uspto-grants-1997_09
Patent number
US05665752

Reaction notes

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