Water → (3,5-Dibromo-4-hydroxy-phenyl)-(2,3-dihydro-pyrido[2,3-b][1,4]oxazin-1-yl)-methanone

HRID 1943627Notes

Reaction equation

HRID 1943627 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH:8]=[C:9]([Br:12])[C:10]=1[OH:11])[C:5]([OH:7])=O.S(Cl)(Cl)=O.[NH:17]1[CH2:22][CH2:21][O:20][C:19]2[N:23]=[CH:24][CH:25]=[CH:26][C:18]1=2.O>CN(C)C(=O)C>[Br:12][C:9]1[CH:8]=[C:4]([C:5]([N:17]2[CH2:22][CH2:21][O:20][C:19]3[N:23]=[CH:24][CH:25]=[CH:26][C:18]2=3)=[O:7])[CH:3]=[C:2]([Br:1])[C:10]=1[OH:11]

Participants

6

Reactant 4

HCID 962WaterHCID 24386Thionyl ChlorideHCID 768573,5-Dibromo-4-hydroxybenzoic acidHCID 151279022,3-Dihydro-1H-pyrido[2,3-b][1,4]oxazine

Product 1

HCID 44610122(3,5-Dibromo-4-hydroxy-phenyl)-(2,3-dihydro-pyrido[2,3-b][1,4]oxazin-1-yl)-methanoneYield 31%

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent2×

Procedure

3,5-dibromo-4-hydroxy-benzoic acid (65 mg, 0.22 mmol) was dissolved in N,N-dimethyl acetamide (1.5 ml) and then cooled to −5□. Thionyl chloride (0.024 ml, 0.33 mmol) was added thereto and stirred at −5□ for 30 minutes. 2,3-dihydro-1H-pyrido[2,3-b][1,4]oxazine dissolved in N,N-dimethyl acetamide (0.7 ml) was added thereto and then stirred at −5□ for 20 minutes, and subsequently stirred at room temperature for 15 hours. Water was added and the mixture was extracted with dichloromethane, and then the (extracted) combined organic layer was dried over anhydrous sodium sulfate (Na2SO4), filtered and evaporated under reduced pressure. The residue was purified by column chromatography on silica eluting with a solvent of n-hexane:ethyl acetate=1:1. The fractions containing the product were collected and evaporated to obtain pale-yellow solid (28 mg, 31%).

Workup

  1. temperaturecooled to −5□
  2. additionwas added
  3. stirringstirred at −5□ for 20 minutes
  4. stirringsubsequently stirred at room temperature for 15 hours
  5. extractionthe mixture was extracted with dichloromethane
  6. extractionthe (extracted)
  7. dry with materialwas dried over anhydrous sodium sulfate (Na2SO4)
  8. filtrationfiltered
  9. customevaporated under reduced pressure
  10. customThe residue was purified by column chromatography on silica eluting with a solvent of n-hexane
  11. additionThe fractions containing the product
  12. customwere collected
  13. customevaporated

Sources & evidence

ORD record
ord-28ef49d20cb3444d987b7537d0cfc5b2
Source dataset
uspto-grants-2013_03
Patent number
US08394792B2

Reaction notes

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