Sodium Hydroxide → HCID 53887608, compound

HRID 363295Notes

Reaction equation

HRID 363295 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([F:16])[C:5]([NH2:15])=[C:6]2[C:10]=1[N:9]([CH2:11][CH3:12])[S:8](=[O:14])(=[O:13])[CH2:7]2.[N:17]([O-])=O.[Na+].[OH-].[Na+]>O.OS(O)(=O)=O.Cl>[Cl:1][C:2]1[C:10]2[N:9]([CH2:11][CH3:12])[S:8](=[O:14])(=[O:13])[CH2:7][C:6]=2[C:5]([NH:15][NH2:17])=[C:4]([F:16])[CH:3]=1

Participants

7

Reactant 3

HCID 14798Sodium HydroxideHCID 23668193Sodium NitriteHCID 53662361HCID 53662361, compound

Product 1

HCID 53887608HCID 53887608, compound

Reagents, catalysts & solvents 3

HCID 313Hydrochloric AcidSolventHCID 962WaterSolvent3×HCID 1118Sulfuric AcidSolvent

Conditions

Temperature
0 °C

Procedure

To a suspension of 7-chloro-1-ethyl-5-fluoro-1,3-dihydro-2,1-benzisothiazol-4-amine 2,2-dioxide (0.5 g, 1.89 mmol) in water (3.1 mL) and H2SO4 (1.65 mL) at 0° C. was added NaNO2 (0.13 g, 1.89 mmol) in water (0.5 mL). The reaction mixture was stirred at 0° C. for 1 h. A solution of SnCL2.H2O (0.85 g, 3.78 mmol) in conc. HCl (3.1 mL) was then added dropwise and the reaction mixture was stirred at room temperature for 12 h. Then 50% aqueous NaOH solution was added until the reaction mixture reached pH 13. The reaction mixture was extracted with ethyl acetate (200 mL) and the organic layer was washed with brine (3×50 mL) and dried (MgSO4). The solvent was removed and the title compound of Step A was isolated by flash chromatography. 1H NMR (CDCl3, 300 MHz): δ 7.04 (d,1H), 5.62 (br s,1H), 4.62 (s,2H), 3.86 (m,2H), 1.26 (t,3H).

Workup

  1. stirringthe reaction mixture was stirred at room temperature for 12 h
  2. extractionThe reaction mixture was extracted with ethyl acetate (200 mL)
  3. washthe organic layer was washed with brine (3×50 mL)
  4. dry with materialdried (MgSO4)
  5. customThe solvent was removed

Sources & evidence

ORD record
ord-2c0ee6586f444a468414c33c57268b1a
Source dataset
uspto-grants-1999_02
Patent number
US05874382

Reaction notes

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