Iodoethane → 6-Bromo-4-ethyl-2,2,7-trimethyl-4H-benzo[1,4]oxazin-3-one

HRID 2239240Notes

Reaction equation

HRID 2239240 reaction equation
[Br:1][C:2]1[C:3]([CH3:15])=[CH:4][C:5]2[O:10][C:9]([CH3:12])([CH3:11])[C:8](=[O:13])[NH:7][C:6]=2[CH:14]=1.[OH-].[K+].[CH2:18](I)[CH3:19]>CS(C)=O>[Br:1][C:2]1[C:3]([CH3:15])=[CH:4][C:5]2[O:10][C:9]([CH3:11])([CH3:12])[C:8](=[O:13])[N:7]([CH2:18][CH3:19])[C:6]=2[CH:14]=1

Participants

5

Reactant 3

HCID 6340IodoethaneHCID 14797Potassium HydroxideHCID 685856146-Bromo-2,2,7-trimethyl-4H-benzo[1,4]oxazin-3-one

Product 1

HCID 685847416-Bromo-4-ethyl-2,2,7-trimethyl-4H-benzo[1,4]oxazin-3-oneYield 95%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent2×

Procedure

Compound 1B (1.0 g, 3.7 mmol) was dissolved in 25 mL of DMSO and added to a prestirred 2.0 M solution of potassium hydroxide (415 mg, 7.4 mmol) in DMSO. Next, ethyl iodide (0.6 mL, 7.4 mmol) was added and the reaction stirred at room temperature overnight. The reaction was quenched with 75 mL of water and extracted with dichloromethane. The combined organic extracts were dried over magnesium sulfate, filtered and excess solvent removed to yield 1.04 g (95%) of desired product. MS (electrospray): mass calculated for C13H16BrNO2, 297.04; m/z found 298, [M+H]+.

Workup

  1. customThe reaction was quenched with 75 mL of water
  2. extractionextracted with dichloromethane
  3. dry with materialThe combined organic extracts were dried over magnesium sulfate
  4. filtrationfiltered
  5. customexcess solvent removed

Sources & evidence

ORD record
ord-699c33e2a6b94064bceaf2f677b9452e
Source dataset
uspto-grants-2010_05
Patent number
US07723326B2

Reaction notes

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