Sodium Hydroxide → HCID 68781949, compound

HRID 2283304Notes

Reaction equation

HRID 2283304 reaction equation
[O:1]([C:8]1[CH:20]=[CH:19][C:11]2[NH:12]C(=O)[NH:14][S:15](=[O:17])(=[O:16])[C:10]=2[CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH-].[Na+]>OS(O)(=O)=O>[NH2:12][C:11]1[CH:19]=[CH:20][C:8]([O:1][C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)=[CH:9][C:10]=1[S:15]([NH2:14])(=[O:16])=[O:17]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 86632006HCID 86632006, compound

Product 1

HCID 68781949HCID 68781949, compoundYield 24.5%

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Conditions

Temperature
105 °C

Procedure

A mixture of 7-phenoxy-1,1-dioxo-1,4-dihydro-2-H-benzo[1,2,4]thiadiazin-3-one (18.0 g, 61.8 mmol) in aqueous H2SO4 (50% v/v, 1 L) was heated at 105° C. for 7 h. The clear solution was then cooled to 0° C. and neutralized using 5N NaOH. The product was extracted with ethyl acetate. The combined extracts were washed with water and concentrated under reduced pressure. The crude product was purified by flash column chromatography using ethyl acetate/hexane (1:1) to afford the title compound (4.0 g, 24%).

Workup

  1. temperatureThe clear solution was then cooled to 0° C.
  2. extractionThe product was extracted with ethyl acetate
  3. washThe combined extracts were washed with water
  4. concentrationconcentrated under reduced pressure
  5. customThe crude product was purified by flash column chromatography

Sources & evidence

ORD record
ord-50068a5b665e48499ba5a4be4517d892
Source dataset
uspto-grants-2015_09
Patent number
US09145380B2

Reaction notes

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