Sodium Hydroxide → 2-Amino-5-methylbenzenesulfonamide

HRID 2283268Notes

Reaction equation

HRID 2283268 reaction equation
[CH3:1][C:2]1[CH:14]=[CH:13][C:5]2[NH:6]C(=O)[NH:8][S:9](=[O:11])(=[O:10])[C:4]=2[CH:3]=1.[OH-].[Na+]>OS(O)(=O)=O>[NH2:6][C:5]1[CH:13]=[CH:14][C:2]([CH3:1])=[CH:3][C:4]=1[S:9]([NH2:8])(=[O:10])=[O:11]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 100818972H-1,2,4-Benzothiadiazin-3(4H)-one, 7-methyl-, 1,1-dioxide

Product 1

HCID 2455842-Amino-5-methylbenzenesulfonamideYield 85%

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Conditions

Temperature
105 °C

Procedure

A mixture of 7-methyl-1,1-dioxo-1,4-dihydro-2-H-benzo[1,2,4]thiadiazin-3-one (7.20 g, 36.36 mmol) in aqueous H2SO4 (50% v/v, 200 mL) was heated at 105° C. for 16 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 4.5 g (85%) of the title compound.

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-d82b1a865f21419fb5aee0cd0d4e5618
Source dataset
uspto-grants-2015_09
Patent number
US09145380B2

Reaction notes

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