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

HRID 2270240Notes

Reaction equation

HRID 2270240 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-141264a054654015bef40aa052e94ffa
Source dataset
uspto-grants-2001_12
Patent number
US06331538B1

Reaction notes

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