(Dimethyl sulfide)trihydroboron → 4-methyl-7-methoxy-3,4-dihydro-2H-[1,4]benzoxazine

HRID 81829Notes

Reaction equation

HRID 81829 reaction equation
[CH3:1][O:2][C:3]1[CH:14]=[CH:13][C:6]2[N:7]([CH3:12])[C:8](=O)[CH2:9][O:10][C:5]=2[CH:4]=1.CSC.B>C1COCC1>[CH3:1][O:2][C:3]1[CH:14]=[CH:13][C:6]2[N:7]([CH3:12])[CH2:8][CH2:9][O:10][C:5]=2[CH:4]=1

Participants

4

Reactant 2

HCID 12423031(Dimethyl sulfide)trihydroboronHCID 233230137-Methoxy-4-methyl-4H-benzo[1,4]oxazin-3-one

Product 1

HCID 136712644-methyl-7-methoxy-3,4-dihydro-2H-[1,4]benzoxazineYield 9.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

7-Methoxy-4-methyl-4H-benzo[1,4]oxazin-3-one (13.07 g, 0.68 mol) was added to 100 mL dry THF, and the reaction mixture was refluxed under nitrogen. Borane-dimethyl sulfide (13.6 mL, 0.136 mol) was added dropwise over one hour, and the reaction mixture was allowed to reflux for two hours. The reaction mixture was cooled and then quenched by addition of 50 mL of 10% aqueous HCl. Precipitate was removed by filtration, and the liquid was concentrated under reduced pressure to give 11.17 g of 7-Methoxy-4-methyl-3,4-dihydro-2H-benzo[1,4]oxazine. (M+H)=180.

Workup

  1. temperaturethe reaction mixture was refluxed under nitrogen
  2. temperatureto reflux for two hours
  3. temperatureThe reaction mixture was cooled
  4. customquenched by addition of 50 mL of 10% aqueous HCl
  5. customPrecipitate was removed by filtration
  6. concentrationthe liquid was concentrated under reduced pressure

Sources & evidence

ORD record
ord-3c367e6b2ae343c7a8075b56fd794fc9
Source dataset
uspto-grants-2014_09
Patent number
US08846705B2

Reaction notes

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