Ozone → HCID 11450134, compound

HRID 1351220Notes

Reaction equation

HRID 1351220 reaction equation
[CH2:1]([C:4]1[C:13]([O:14][CH3:15])=[C:12]([O:16][CH3:17])[CH:11]=[C:10]2[C:5]=1[C:6]([NH:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)=[N:7][CH:8]=[N:9]2)[CH:2]=C.[O:25]=[O+][O-]>CO>[CH3:15][O:14][C:13]1[C:12]([O:16][CH3:17])=[CH:11][C:10]2=[C:5]3[C:4]=1[CH2:1][CH:2]([OH:25])[N:18]([C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)[C:6]3=[N:7][CH:8]=[N:9]2

Participants

4

Reactant 2

HCID 24823OzoneHCID 11174663HCID 11174663, compound

Product 1

HCID 11450134HCID 11450134, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of (5-allyl-6,7-dimethoxy-quinazolin-4-yl)-phenyl-amine (0.35 g, 1.09 mmol) (from Example 15, Step E ,supra) in methanol (50 mL) at −78° C. was passed a continuous stream of O3 until the color of the solution became blue. The reaction solution was then purged with argon, and methyl sulfide (5 mL) (Aldrich) was added. The reaction mixture was slowly warmed to room temperature and stirred overnight. The solution was concentrated, the residue was dried in vacuo to give the desired 7,8-dimethoxy-4-phenyl-5,6-dihydro-4H-1,3,4-triaza-phenalen-5-ol as a crude yellow solid. (Yield 0.17 g, 48%).

Workup

  1. customat −78° C.
  2. customThe reaction solution was then purged with argon, and methyl sulfide (5 mL) (Aldrich)
  3. additionwas added
  4. concentrationThe solution was concentrated
  5. customthe residue was dried in vacuo

Sources & evidence

ORD record
ord-c1ae11e5dd894b57be998ce9e35b5388
Source dataset
uspto-grants-2007_05
Patent number
US07217717B2

Reaction notes

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