Water → HCID 14151565, compound

HRID 2165998Notes

Reaction equation

HRID 2165998 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-d9b0f5ada74b43739e4425787d83cdc9
Source dataset
uspto-grants-1990_07
Patent number
US04943314

Reaction notes

Loading…