Lithium → 7,8-Difluoro-3,4-dihydro-2H-1,4-benzothiazine

HRID 2416850Notes

Reaction equation

HRID 2416850 reaction equation
[F:1][C:2]1[CH:12]=[CH:11][C:5]2[NH:6][C:7](=O)[CH2:8][S:9][C:4]=2[C:3]=1[F:13].[Li]>C1COCC1>[F:1][C:2]1[CH:12]=[CH:11][C:5]2[NH:6][CH2:7][CH2:8][S:9][C:4]=2[C:3]=1[F:13]

Participants

4

Reactant 2

HCID 3028194LithiumHCID 22632969HCID 22632969, compound

Product 1

HCID 226329587,8-Difluoro-3,4-dihydro-2H-1,4-benzothiazineYield 104%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 7,8-difluoro-4H-benzo[1,4]thiazin-3-one (Example L-3, 2.27 g, 11.3 mmol) in THF (100 mL) was reacted with lithium aluminumhydride (1.07 g, 28.2 mmol) under an N2 atmosphere and heated to reflux overnight. The mixture was cooled and quenched with 1.0N HCl and extracted with ethyl acetate. The organic layers were combined, dried with sodium sulfate, and concentrated to provide 2.2 g of the title compound as an oil.

Workup

  1. temperatureheated
  2. temperatureto reflux overnight
  3. temperatureThe mixture was cooled
  4. customquenched with 1.0N HCl
  5. extractionextracted with ethyl acetate
  6. dry with materialdried with sodium sulfate
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-6f517e4540994d20b33bf66295527942
Source dataset
uspto-grants-2004_11
Patent number
US06825199B2

Reaction notes

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