Imidazole → HCID 23505607, compound

HRID 1884389Notes

Reaction equation

HRID 1884389 reaction equation
Cl[CH2:2][C:3]1[N+:12]([O-:13])=[C:11]([C:14]2[CH:19]=[CH:18][C:17]3[O:20][CH2:21][O:22][C:16]=3[CH:15]=2)[C:10]2[C:5](=[CH:6][C:7]3[O:25][CH2:24][O:23][C:8]=3[CH:9]=2)[N:4]=1.[NH:26]1[CH:30]=[CH:29][N:28]=[CH:27]1>CN(C=O)C>[N:26]1([CH2:2][C:3]2[N+:12]([O-:13])=[C:11]([C:14]3[CH:19]=[CH:18][C:17]4[O:20][CH2:21][O:22][C:16]=4[CH:15]=3)[C:10]3[C:5](=[CH:6][C:7]4[O:25][CH2:24][O:23][C:8]=4[CH:9]=3)[N:4]=2)[CH:30]=[CH:29][N:28]=[CH:27]1

Participants

4

Reactant 2

HCID 795ImidazoleHCID 23505617HCID 23505617, compound

Product 1

HCID 23505607HCID 23505607, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
85 °C

Procedure

To a suspension of 2-chloromethyl-6,7-methylenedioxy-4-(3,4-methylenedioxyphenyl)quinazoline-3-oxide (192 mg, 0.53 mmol), in dry DMF (3 mL), was added imidazole (142 mg, 2.1 mmol). The mixture was stirred at 85° C. for 1.5 h and left at rt for 15 h. DMF was removed and the mixture was poured into ice-water. The precipitated solid was extracted with EtOAc. The organic layer was washed with water, brine and dried over anhydrous MgSO4. It was filtered and the solvent was removed to yield the title compound as off white solid (100 mg); mp 212-217° C. 1H NMR (CDCl3) 7.76 (s, 1H), 7.00-7.21 (m, 5H), 6.80 (s 1H), 6.13 (s, 2H), 6.08 (s, 2H), 5.63 (s, 2H).

Workup

  1. waitleft at rt for 15 h
  2. customDMF was removed
  3. additionthe mixture was poured into ice-water
  4. extractionThe precipitated solid was extracted with EtOAc
  5. washThe organic layer was washed with water, brine
  6. dry with materialdried over anhydrous MgSO4
  7. filtrationIt was filtered
  8. customthe solvent was removed

Sources & evidence

ORD record
ord-f002936e445f4a90b25a037597305a4f
Source dataset
uspto-grants-2004_07
Patent number
US06765006B2

Reaction notes

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