Hydrochloric Acid → HCID 66936677, compound

HRID 1943714Notes

Reaction equation

HRID 1943714 reaction equation
[NH:1]1[C:14]2[CH:13]=[N:12][C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[C:5]=2[O:4][CH2:3][CH2:2]1.[Br:15][C:16]1[CH:17]=[C:18]([CH:22]=[C:23]([Br:27])[C:24]=1[O:25][CH3:26])[C:19](Cl)=[O:20].C(N(CC)CC)C.Cl>ClCCl>[Br:15][C:16]1[CH:17]=[C:18]([C:19]([N:1]2[C:14]3[CH:13]=[N:12][C:11]4[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=4)[C:5]=3[O:4][CH2:3][CH2:2]2)=[O:20])[CH:22]=[C:23]([Br:27])[C:24]=1[O:25][CH3:26]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 8471TriethylamineHCID 337796303,5-Dibromo-4-methoxybenzoyl chlorideHCID 66936850HCID 66936850, compound

Product 1

HCID 66936677HCID 66936677, compoundYield 86%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

In a 10 ml flask, 2,3-dihydro-1H-4-oxa-1,9-diaza-phenanthrene (50 mg, 0.269 mmol) and 3,5-dibromo-4-methoxy-benzoyl chloride (88 mg, 0.269 mmol) were dissolved in dichloromethane. Triethylamine (0.51 ml, 3.7 mmol) was added thereto and then stirred at room temperature for 3 hours. After neutralizing with 1N hydrochloric acid solution, the mixture was extracted with dichloromethane, and the combined organic layer was dried over anhydrous sodium sulfate (Na2SO4), filtered and evaporated under reduced pressure. The residue was purified by column chromatography on amine silica eluting with a solvent of dichloromethane:methanol=20:1. The fractions containing the product were collected and evaporated to obtain the target compound as yellow solid (110 mg, 86%).

Workup

  1. extractionthe mixture was extracted with dichloromethane
  2. dry with materialthe combined organic layer was dried over anhydrous sodium sulfate (Na2SO4)
  3. filtrationfiltered
  4. customevaporated under reduced pressure
  5. customThe residue was purified by column chromatography on amine silica eluting with a solvent of dichloromethane
  6. additionThe fractions containing the product
  7. customwere collected
  8. customevaporated

Sources & evidence

ORD record
ord-65ef842c831b4f9c9b93c1f3f41b395c
Source dataset
uspto-grants-2013_03
Patent number
US08394792B2

Reaction notes

Loading…