Water → HCID 14151565, compound

HRID 230992Notes

Reaction equation

HRID 230992 reaction equation
[C:1]([CH2:9][C:10]([NH:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)=[O:11])(=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:19]([NH2:23])[CH2:20][CH2:21][CH3:22].O.C(C1(C)[O:32][C:31](=O)[CH:30]=[C:29]([CH3:34])O1)C>C(O)(=O)C.C1(C)C=CC=CC=1>[CH2:19]([N:23]1[C:29]([CH3:34])=[CH:30][C:31](=[O:32])[C:9]([C:10]([NH:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[O:11])=[C:1]1[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)[CH2:20][CH2:21][CH3:22]

Participants

7

Reactant 4

HCID 962WaterHCID 8007Butylamine2×HCID 703983-Oxo-3-phenylpropionanilideHCID 10534915HCID 10534915, compound

Product 1

HCID 14151565HCID 14151565, compoundYield 55.9%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidCatalystHCID 1140TolueneSolvent2×

Procedure

A mixture of 4.42 g (18.47 mmol) of α-benzoylacetanilide, 1.89 g (25.84 mmol) of n-butylamine, one drop of acetic acid and 25 ml of toluene was refluxed for 1.5 hours, while the resulted water and excess of butylamine were removed through a Dean-Stark's water separator, together with about 12 ml of toluene. While heating, to the mixture was dropwise added a solution of 7.2 g (46.18 mmol) of 2-ethyl-2,6-dimethyl-4H-1,3-dioxin-4-one in 16 ml of toluene within about 30 minutes and after the resulted mixture was refluxed for forty minutes, it was cooled to room temperature. The crystals precipitated was separated by filtration and dried under vacuo to afford 3.72 g of the title compound having mp. 189.5°-193° C.

Workup

  1. customwere removed through a Dean-Stark's water
  2. temperatureWhile heating, to the mixture
  3. temperatureafter the resulted mixture was refluxed for forty minutes
  4. customThe crystals precipitated
  5. customwas separated by filtration
  6. customdried under vacuo

Sources & evidence

ORD record
ord-9324f0bf0e974a2b8a57678ed1f3ab72
Source dataset
uspto-grants-1989_07
Patent number
US04844732

Reaction notes

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