p-Toluenesulfonic acid → HCID 58709769, compound

HRID 2375911Notes

Reaction equation

HRID 2375911 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([C:10](=O)[CH2:11][N:12]2C(=O)[C:20]3[C:15](=CC=CC=3)[N:14]=[CH:13]2)[CH:7]=[CH:8][CH:9]=1)([O-:3])=[O:2].[CH3:24][N:25](C)[CH2:26]CN.C1(C)C=CC(S(O)(=O)=O)=CC=1.C([O-])(O)=O.[Na+]>O>[CH3:24][N:25]([CH3:26])[CH2:20][CH2:15][N:14]1[C:10]([C:6]2[CH:7]=[CH:8][CH:9]=[C:4]([N+:1]([O-:3])=[O:2])[CH:5]=2)=[CH:11][N:12]=[CH:13]1

Participants

6

Reactant 4

HCID 6101p-Toluenesulfonic acidHCID 66053N,N-DimethylethylenediamineHCID 516892Sodium BicarbonateHCID 1280267HCID 1280267, compound

Product 1

HCID 58709769HCID 58709769, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A stirred mixture of 3-[2-(3-nitrophenyl)-2-oxoethyl]-3H-quinazolin-4-one (2.00 g, 6.47 mmol), N,N-dimethyl-1,2-ethanediamine (2.28 g, 25.9 mmol), and p-toluenesulfonic acid (2.23 g, 12.9 mmol) in xylenes (150 mL) was refluxed for 48 h. After cooling to rt, water (20 mL) and sat. NaHCO3 (aq) (15 mL) were added. Layers were separated, and the aqueous phase was extracted with EtOAc (3×50 mL). The combined organic phases were dried over MgSO4, filtered, concentrated, and purified by silica gel chromatography (8% MeOH in CH2Cl2) to afford the desired product. 1H-NMR (CD3OD, 400 MHz): δ=2.15 (s, 6H), 2.54 (t, J=7.2 Hz, 2H), 4.22 (t, J=6.8 Hz, 2H), 7.15 (d, J=1.2 Hz, 1H), 7.74 (t, J=8.0 Hz, 1H), 7.89 (dt, J=2.4, 7.6 Hz, 1H), 7.90 (s, 1H), 8.24-8.26 (m, 1H), 8.30 (s, 1H). MS (ES+): m/z 261.24 [MH+]. HPLC: tR=0.49 and 0.71 min (ZQ2000, polar—5 min).

Workup

  1. temperaturewas refluxed for 48 h
  2. customLayers were separated
  3. extractionthe aqueous phase was extracted with EtOAc (3×50 mL)
  4. dry with materialThe combined organic phases were dried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. custompurified by silica gel chromatography (8% MeOH in CH2Cl2)

Sources & evidence

ORD record
ord-f9c38421d96e4d0cbc317795e8be666b
Source dataset
uspto-grants-2008_12
Patent number
US07465726B2

Reaction notes

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