Diketene → HCID 21419830, compound

HRID 441277Notes

Reaction equation

HRID 441277 reaction equation
[CH2:1]=[C:2]1[O:6][C:4](=[O:5])[CH2:3]1.[NH2:7][C:8]1[CH:9]=[C:10]([CH:18]=[CH:19][CH:20]=1)[NH:11][C:12](=[O:17])[CH2:13][CH2:14][CH2:15][CH3:16]>C1C=CC=CC=1>[C:12]([NH:11][C:10]1[CH:9]=[C:8]([CH:20]=[CH:19][CH:18]=1)[NH:7][C:4](=[O:5])[CH2:3][C:2](=[O:6])[CH3:1])(=[O:17])[CH2:13][CH2:14][CH2:15][CH3:16]

Participants

4

Reactant 2

HCID 12661DiketeneHCID 5138852N-(3-aminophenyl)pentanamide

Product 1

HCID 21419830HCID 21419830, compoundYield 24.6%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Conditions

Temperature
20 °C

Procedure

42 g of diketene were added to a mixture of 96 g of m-aminovaleranilide in 400 ml of benzene and the mixture was stirred for 16 hours at 20° C. The benzene was decanted and the residue was added to refluxing benzene. The mixture was treated with activated carbon and filtered to obtain raw m-valeramido-acetylacetanilide melting at 90° C. Crystallization from ethyl acetate yielded 34 g of pure m-valeramido-acetylacetanilide melting at 116° C.

Workup

  1. customThe benzene was decanted
  2. additionthe residue was added
  3. temperatureto refluxing benzene
  4. additionThe mixture was treated with activated carbon
  5. filtrationfiltered
  6. customto obtain raw m-valeramido-acetylacetanilide melting at 90° C
  7. customCrystallization from ethyl acetate

Sources & evidence

ORD record
ord-8d826342c94249ddbeca380895b4516c
Source dataset
uspto-grants-1977_08
Patent number
US04039316

Reaction notes

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