Sodium Bicarbonate → HCID 67285873, compound

HRID 1618643Notes

Reaction equation

HRID 1618643 reaction equation
[C:1]([N:4]1[C:9]2[CH:10]=[C:11]([N+:14]([O-])=O)[CH:12]=[CH:13][C:8]=2[S:7](=[O:18])(=[O:17])[CH2:6][CH2:5]1)(=[O:3])[CH3:2].C(=O)(O)[O-].[Na+]>CCOC(C)=O>[C:1]([N:4]1[C:9]2[CH:10]=[C:11]([NH2:14])[CH:12]=[CH:13][C:8]=2[S:7](=[O:17])(=[O:18])[CH2:6][CH2:5]1)(=[O:3])[CH3:2]

Participants

4

Reactant 2

HCID 516892Sodium BicarbonateHCID 67285399HCID 67285399, compound

Product 1

HCID 67285873HCID 67285873, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To a suspension of 4-acetyl-6-nitro-3,4-dihydro-2H-1,4-benzothiazine 1,1-dioxide (1.6 g, 5.92 mmol) in EtOAc (21 mL) was added SnCl2-2H2O (6.68 g, 29.6 mmol) and the mixture was heated at reflux for 1.5 h. After this time the reaction mixture was cooled to rt and treated with 2N sodium bicarbonate (30 mL). The resulting solid was filtered and the aqueous layer was extracted with EtOAc. The combined organic layers were washed with brine, dried over Mg2SO4, filtered and evaporated in vacuo to give 4-acetyl-3,4-dihydro-2H-1,4-benzothiazin-6-amine 1,1-dioxide. Mass Spectrum (ESI) m/e=241 (M+1).

Workup

  1. temperaturethe mixture was heated
  2. temperatureat reflux for 1.5 h
  3. filtrationThe resulting solid was filtered
  4. extractionthe aqueous layer was extracted with EtOAc
  5. washThe combined organic layers were washed with brine
  6. dry with materialdried over Mg2SO4
  7. filtrationfiltered
  8. customevaporated in vacuo

Sources & evidence

ORD record
ord-29ad0df35d5345dbaa690e1993e00ba7
Source dataset
uspto-grants-2014_07
Patent number
US08765940B2

Reaction notes

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