Sodium Iodide → HCID 22648095, compound

HRID 394083Notes

Reaction equation

HRID 394083 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([Cl:8])[C:3]=1[N:9]1[C:18]2[C:13](=[C:14]([C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=3[Cl:26])[CH:15]=[C:16]([OH:19])[CH:17]=2)[CH2:12][NH:11][C:10]1=[O:27].C(=O)([O-])[O-].[K+].[K+].[CH2:34](Cl)[CH:35]=[CH2:36].[I-].[Na+]>CC(C)=O>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([Cl:8])[C:3]=1[N:9]1[C:18]2[C:13](=[C:14]([C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=3[Cl:26])[CH:15]=[C:16]([O:19][CH2:36][CH:35]=[CH2:34])[CH:17]=2)[CH2:12][NH:11][C:10]1=[O:27]

Participants

6

Reactant 4

HCID 5238Sodium IodideHCID 7850Allyl chlorideHCID 11430Potassium CarbonateHCID 22647873HCID 22647873, compound2×

Product 1

HCID 22648095HCID 22648095, compound

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A solution containing 1-(2,6 dichlorophenyl)-5-(2-chlorophenyl)-7-hydroxy-3,4-dihydro-2(1H)-quinazolinone (259 mg, 0.617 mmol) (INTERMEDIATE 49), potassium carbonate (300 mg, 2.2 mmol), allyl chloride (0.45 mL, 5.53 mmol) and sodium iodide (87 mg, 0.58 mmol) in 15 mL acetone was refluxed for seven hours. The solution was concentrated and the residue partitioned between EtOAc and water. The organic phase was washed with brine, dried over Na2SO4, filtered and concentrated. The residue was purified by silica gel chromatography using 2% acetone in DCM to give 1-(2,6-dichlorophenyl)-5-(2chlorophenyl)-7-allyloxy-3,4-dihydro-2(1H)-quinazolinone. 1H NMR(CDCl3, 500 MHz): δ 4.18 (d, 1H, 14.2 Hz), 4.34 (d, 1H, J=14.2 Hz), 4.40 (app d, 2H, J=5.5 Hz), 5.20-5.32(m, 2H), 5.77 (d, 1H, J=2.3 Hz), 5.82 (s, 1H), 5.90-6.00 (m, 1H), 6.44 (d, 1H, J=2.3 Hz), 7.27-7.31 (m, 1H), 7.32-7.38 (m, 3H), 7.48-7.52 (m, 3H). MS(ES) 459 (M+H); LC 1: 3.30 min.

Workup

  1. temperaturewas refluxed for seven hours
  2. concentrationThe solution was concentrated
  3. customthe residue partitioned between EtOAc and water
  4. washThe organic phase was washed with brine
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe residue was purified by silica gel chromatography

Sources & evidence

ORD record
ord-27e4b531f59a4870bad4302701036852
Source dataset
uspto-grants-2004_10
Patent number
US06809199B2

Reaction notes

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