Ammonia → 3192-06-1

HRID 58860Notes

Reaction equation

HRID 58860 reaction equation
[Li].C([N:9]1[C:14]2[CH:15]=[CH:16][CH:17]=[CH:18][C:13]=2[CH:12]=[CH:11][S:10]1(=[O:20])=[O:19])C1C=CC=CC=1.CCO.N>C1COCC1>[NH:9]1[C:14]2[CH:15]=[CH:16][CH:17]=[CH:18][C:13]=2[CH2:12][CH2:11][S:10]1(=[O:19])=[O:20]

Participants

6

Reactant 4

HCID 222AmmoniaHCID 702EthanolHCID 3028194LithiumHCID 101859068HCID 101859068, compound

Product 1

HCID 122033353192-06-1Yield 34.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Freshly polished lithium flakes (2.0 g, 0.28 mol) were added to a solution of 1-benzyl-1H-benzo[c][1,2]thiazine 2,2-dioxide (6.5 g, 24 mmol) in THF (120 mL)/EtOH (12 mL) and liquid NH3 (150 mL) at −40° C. with stirring over 0.5 h. The reaction was quenched with NH4Cl powder (10 g). Water (200 mL) and EtOAc (200 mL) were added. The two layers were separated and the aqueous phase was extracted with EtOAc (100 mL×3). The combined organic phases were washed with brine (200 mL×3), dried over anhydrous sodium sulfate, and concentrated. The residue was purified by flash column chromatography on silica gel (EtOAc/hexane=1:4) to afford 3,4-dihydro-1H-benzo[c][1,2]thiazine 2,2-dioxide (1.5 g, 34% yield).

Workup

  1. customThe reaction was quenched with NH4Cl powder (10 g)
  2. additionWater (200 mL) and EtOAc (200 mL) were added
  3. customThe two layers were separated
  4. extractionthe aqueous phase was extracted with EtOAc (100 mL×3)
  5. washThe combined organic phases were washed with brine (200 mL×3)
  6. dry with materialdried over anhydrous sodium sulfate
  7. concentrationconcentrated
  8. customThe residue was purified by flash column chromatography on silica gel (EtOAc/hexane=1:4)

Sources & evidence

ORD record
ord-28944344bd9640e2bb11ed3a14d15f1f
Source dataset
uspto-grants-2016_09
Patent number
US09434761B2

Reaction notes

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