Acetyl chloride → HCID 13194658, compound

HRID 464435Notes

Reaction equation

HRID 464435 reaction equation
[Cl:1][C:2]1[CH:14]=[CH:13][C:5]([C:6]([NH:8][N:9]=[C:10]([CH3:12])[CH3:11])=[O:7])=[CH:4][CH:3]=1.C(N(CC)CC)C.[C:22](Cl)(=[O:24])[CH3:23]>O1CCCC1>[Cl:1][C:2]1[CH:14]=[CH:13][C:5]([C:6]([N:8]([C:22](=[O:24])[CH3:23])[N:9]=[C:10]([CH3:11])[CH3:12])=[O:7])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 6367Acetyl chlorideHCID 8471TriethylamineHCID 3516324-chloro-N-(propan-2-ylideneamino)benzamide

Product 1

HCID 13194658HCID 13194658, compoundYield 82%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

10.5 g of 1-p-chlorobenzoyl-2-isopropylidene hydrazine, 5.3 g of triethylamine and 100 ml of tetrahydrofuran were placed in a 200 ml round-bottom flask, and while stirring with ice-water cooling, 3.9 of acetylchloride was dropped gradually. After dropping, the mixture was heated at reflux for one hour so as to complete the reaction. The reaction mixture was cooled to room temperature and the separated salts were filtered off, and then the filtrate was concentrated to obtain yellow brown crystals, which were then recrystallized from a mixed solvent of hexane/acetone to yield 10.4 g (82%) of yellow crystalline 1-p-chlorobenzoyl-1-acetyl-2-isopropylidene hydrazine having a melting point of 73°-74° C.

Workup

  1. additionwas dropped gradually
  2. temperaturethe mixture was heated
  3. temperatureat reflux for one hour so as
  4. customthe reaction
  5. filtrationthe separated salts were filtered off
  6. concentrationthe filtrate was concentrated
  7. customto obtain yellow brown crystals, which
  8. customwere then recrystallized from a mixed solvent of hexane/acetone

Sources & evidence

ORD record
ord-62146071440d4092990a46123d4b731d
Source dataset
uspto-grants-1985_10
Patent number
US04547524

Reaction notes

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