Sodium hydride → HCID 86650559, compound

HRID 1943671Notes

Reaction equation

HRID 1943671 reaction equation
[Cl:1][C:2]1[C:11]2[NH:10][CH2:9][CH2:8][O:7][C:6]=2[CH:5]=[CH:4][N:3]=1.[H-].[Na+].[Br:14][C:15]1[CH:16]=[C:17]([CH:21]=[C:22]([Br:26])[C:23]=1[O:24][CH3:25])[C:18](Cl)=[O:19]>C(OCCCC)CCC>[Cl:1][C:2]1[C:11]2[N:10]([C:18]([C:17]3[CH:21]=[C:22]([Br:26])[C:23]([O:24][CH3:25])=[C:15]([Br:14])[CH:16]=3)=[O:19])[CH2:9][CH2:8][O:7][C:6]=2[CH:5]=[CH:4][N:3]=1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 337796303,5-Dibromo-4-methoxybenzoyl chlorideHCID 707007455-Chloro-3,4-dihydro-2H-pyrido[4,3-b][1,4]oxazine

Product 1

HCID 86650559HCID 86650559, compoundYield 50%

Reagents, catalysts & solvents 1

HCID 8909Butyl etherSolvent

Procedure

In a 50 ml flask equipped with a reflux apparatus, 5-chloro-3,4-dihydro-2H-pyrido[4,3-b][1,4]oxazine (890 mg, 5.22 mmol) was dissolved in butyl ether (20 ml), and 60% sodium hydride in mineral oil (250 mg, 6.26 mmol) was added and stirred at 1250 for 3.5 hours. The mixture was cooled to room temperature and 3,5-dibromo-4-methoxy-benzoyl chloride (2.06 g, 6.26 mmol) was added thereto and then stirred at 1250 for 24 hours. The mixture was cooled to room temperature and filtered and evaporated under reduced pressure. The residue was washed with methanol and dried under reduced pressure to obtain white solid (1.2 g, 50%).

Workup

  1. stirringstirred at 1250 for 24 hours
  2. temperatureThe mixture was cooled to room temperature
  3. filtrationfiltered
  4. customevaporated under reduced pressure
  5. washThe residue was washed with methanol
  6. customdried under reduced pressure

Sources & evidence

ORD record
ord-f64b2efa4f3943b8a0e4a6f6d37c7a29
Source dataset
uspto-grants-2013_03
Patent number
US08394792B2

Reaction notes

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