Methyl iodide → 7-Bromo-1,4,4-trimethyl-3,1-benzoxazin-2-one

HRID 2209290Notes

Reaction equation

HRID 2209290 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]2[C:10]([CH3:12])([CH3:11])[O:9][C:8](=[O:13])[NH:7][C:6]=2[CH:14]=1.[CH3:15][Si]([N-][Si](C)(C)C)(C)C.[Na+].CI>CN(C=O)C.C1COCC1>[Br:1][C:2]1[CH:3]=[CH:4][C:5]2[C:10]([CH3:11])([CH3:12])[O:9][C:8](=[O:13])[N:7]([CH3:15])[C:6]=2[CH:14]=1

Participants

6

Reactant 3

HCID 6328Methyl iodideHCID 2724254Sodium bis(trimethylsilyl)amideHCID 468564867-bromo-4,4-dimethyl-1H-benzo[d][1,3]oxazin-2(4H)-one

Product 1

HCID 1178431767-Bromo-1,4,4-trimethyl-3,1-benzoxazin-2-one

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8028TetrahydrofuranSolvent

Procedure

Into the solution of 7-bromo-4,4-dimethyl-1H-benzo[d][1,3]oxazin-2(4H)-one 7.37 (1.35 g) in DMF (20 mL) was added 1M solution of NaHMDS in THF (7 mL) at rt. After 30 min., MeI (0.85 g) was added. After overnight stirring, the reaction mixture was extracted with ethyl acetate and washed with brine, and dried with dry agent. After removal of the solvent, the residue was crystallized from mixture of DCM and Hexane to provide 1.2 g of 7-bromo-1,4,4-trimethyl-1H-benzo[d][1,3]oxazin-2(4H)-one 7.38 was synthesized.

Workup

  1. extractionthe reaction mixture was extracted with ethyl acetate
  2. washwashed with brine
  3. customdried
  4. customwith dry agent
  5. customAfter removal of the solvent
  6. customthe residue was crystallized from mixture of DCM and Hexane

Sources & evidence

ORD record
ord-6f60589751744e599d97717392b38cd7
Source dataset
uspto-grants-2016_06
Patent number
US09376441B2

Reaction notes

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