Toluene → HCID 22345230, compound

HRID 2193956Notes

Reaction equation

HRID 2193956 reaction equation
C([C:8]1[C:17](=[O:18])[C:16]2[C:11](=[CH:12][C:13]([Cl:19])=[CH:14][CH:15]=2)[O:10][C:9]=1[CH:20]([NH:24][CH2:25][CH2:26][NH:27][C:28](=O)[C:29]1[CH:34]=[CH:33][C:32]([CH3:35])=[CH:31][CH:30]=1)[CH:21]([CH3:23])[CH3:22])C1C=CC=CC=1.P(Cl)(Cl)(Cl)=O.[C:42]1([CH3:48])[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=1>>[CH2:48]([C:8]1[C:17](=[O:18])[C:16]2[C:11](=[CH:12][C:13]([Cl:19])=[CH:14][CH:15]=2)[O:10][C:9]=1[CH:20]([N:24]1[CH2:25][CH2:26][N:27]=[C:28]1[C:29]1[CH:34]=[CH:33][C:32]([CH3:35])=[CH:31][CH:30]=1)[CH:21]([CH3:23])[CH3:22])[C:42]1[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=1

Participants

4

Reactant 3

HCID 1140TolueneHCID 24813Phosphorus oxychlorideHCID 66756024HCID 66756024, compound

Product 1

HCID 22345230HCID 22345230, compoundYield 50%

Conditions

Temperature
85 °C

Procedure

A mixture of N-{2-[1-(3-benzyl-7-chloro-4-oxo-4H-chromen-2-yl)-2-methyl-propylamino]-ethyl}-4-methyl-benzamide (2.8 g, 5.5 mmol) and phosphorus oxychloride (9.4 mL, 100 mmol) in toluene (60 mL) was heated at 85° C. for 7 hours, then heated at reflux for 1 hour. The reaction was concentrated and the residual phosphorus oxychloride removed by toluene azeotrope. The residue was diluted with ethyl acetate (100 mL) and washed with saturated sodium bicarbonate (100 mL) and brine (100 mL), dried over magnesium sulfate, and concentrated. The resultant residue was purified by flash chromatography (0→8% methanol/methylene chloride) to give 1.4 g (50%) of the title compound. MS (ES+) m/e 485 [M+H]

Workup

  1. temperatureheated
  2. temperatureat reflux for 1 hour
  3. concentrationThe reaction was concentrated
  4. customthe residual phosphorus oxychloride removed by toluene azeotrope
  5. additionThe residue was diluted with ethyl acetate (100 mL)
  6. washwashed with saturated sodium bicarbonate (100 mL) and brine (100 mL)
  7. dry with materialdried over magnesium sulfate
  8. concentrationconcentrated
  9. customThe resultant residue was purified by flash chromatography (0→8% methanol/methylene chloride)

Sources & evidence

ORD record
ord-8ebf864229784908a1b7515ba82ee985
Source dataset
uspto-grants-2012_12
Patent number
US08329928B2

Reaction notes

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