Hydrochloric Acid → HCID 67379097, compound

HRID 717785Notes

Reaction equation

HRID 717785 reaction equation
[CH3:1][C:2]1[CH:3]=[CH:4][C:5]2[NH:10][C:9](=O)[CH:8]([C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=3)[O:7][C:6]=2[CH:18]=1.B.CSC.Cl.[OH-].[Na+]>C1COCC1>[CH3:1][C:2]1[CH:3]=[CH:4][C:5]2[NH:10][CH2:9][CH:8]([C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=3)[O:7][C:6]=2[CH:18]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 11837324HCID 11837324, compoundHCID 12423031(Dimethyl sulfide)trihydroboron

Product 1

HCID 67379097HCID 67379097, compoundYield 53.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

7-Methyl-2-phenyl-2H-benzo[b][1,4]oxazin-3(4H)-one (2.2 g) was dissolved in THF (40 mL), and the mixture was cooled to 0° C. Borane-DMS (2.7 g) was added dropwise under inert atmosphere. After addition, the reaction mixture was heated to 70° C. for 4 h. The reaction was monitored by TLC. After completion of reaction, the mixture was cooled, and to it was added 1N HCl (50 mL). The reaction mixture was basified to pH 12 with NaOH solution and then extracted with EtOAc (3×100 mL). The organic layer was dried over sodium sulfate and concentrated under reduced pressure. The crude product was purified by column chromatography using silica (100-200 mesh size) using 8% EtOAc/Hexane as eluent, to provide 1.1 g of pure product.

Workup

  1. additionAfter addition
  2. temperaturethe reaction mixture was heated to 70° C. for 4 h
  3. customAfter completion of reaction
  4. temperaturethe mixture was cooled
  5. extractionextracted with EtOAc (3×100 mL)
  6. dry with materialThe organic layer was dried over sodium sulfate
  7. concentrationconcentrated under reduced pressure
  8. customThe crude product was purified by column chromatography

Sources & evidence

ORD record
ord-c52710085bdc4fcca33b8a25a9f43151
Source dataset
uspto-grants-2015_11
Patent number
US09193728B2

Reaction notes

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