Diethyl Ether → HCID 17777162, compound

HRID 583082Notes

Reaction equation

HRID 583082 reaction equation
N[CH2:2][C:3]([C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)=O.[S:11]([NH2:15])([NH2:14])(=[O:13])=[O:12].COCCO[CH2:21][CH2:22]OC.[OH-].[Na+].[CH3:27]COCC>>[CH3:2][CH:3]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:10]=2[N:15]([CH2:27][CH:21]=[CH2:22])[S:11](=[O:13])(=[O:12])[NH:14]1

Participants

6

Reactant 5

HCID 3283Diethyl EtherHCID 8150DiglymeHCID 11952PhenacylamineHCID 14798Sodium HydroxideHCID 82267Sulfamide

Product 1

HCID 17777162HCID 17777162, compound

Conditions

Temperature
150 °C

Procedure

2-Aminoacetophenone(5.6 g, 41.5 mmol)and sulfamide (4 g, 41.5 mm) were added to diglyme (70 ml, dried over 4A molecular sieves) and the solution heated under nitrogen at 150° C. After 1 hour a solid forms but heating was continued for 2 hours in total. After cooling, ether was added followed by 2N sodium hydroxide which dissolved the solid formed. The aqueous phase was collected, diluted with ethanol and (prop-2-en-1-yl) bromide (8 ml) added, stirring being continued overnight. After concentration under vacuo the residue was partitioned between water and ethyl acetate. The organic phase was collected, dried, over magnesium sulfate, filtered and the solvent evaporated under reduced pressure to yield a yellow oil, 3,4-dihydro-4-methyl-1-(prop-2-en-1-yl)-1H-2,1,3-benzothiadiazine-2,2-dioxide. 3,4-Dihydro-4-methyl-1-(prop-2-en-1-yl)-1H-2,1,3-benzothiadiazine-2,2-dioxide(2.4 g, 10 mmol) was dissolved in dry tetrahydrofuran (40 ml) under nitrogen and the solution cooled to -78° C. in an acetone/dry ice bath. Methyl magnesium bromide (5 ml, 3M solution in ether) was added at this temperature and kept for 30 minutes when it was allowed to come to room temperature. After stirring for 2 hours, water was added and the solution concentrated. Partitioning between ethyl acetate and dilute HCl(aq) and collection of the organic extracts followed by drying, filtering and removal of solvent gave a product showing 75% conversion to product. Column chromatography eluting with ethyl acetate/hexane gave product, 3,4-dihydro-4,4-dimethyl-1-(prop-2-en-1-yl)-1H-2,1,3-benzothiadiazine-2,2-dioxide. This compound (1.85 g, 7.3 mmol) was dissolved in N-methylpyrrolidine (30 ml) under nitrogen and sodium hydride (350 mg) was added at room temperature resulting in a vigorous effervescence. After the gas evolution had subsided (30 minutes), methyl iodide (300 mg) was added and the solution stirred overnight. The reaction was poured onto water and extracted with ethyl acetate(3×50 ml). Organic phase was washed with water (2×100 ml), dried, filtered and vacced to an oil, 3,4-dihydro-1-(prop-2-en-1-yl)-3,4,4-trimethyl-1H-2,1,3-benzothiadiazine-2,2-dioxide.

Workup

  1. temperatureheating
  2. waitwas continued for 2 hours
  3. temperatureAfter cooling
  4. dissolutiondissolved the solid
  5. customformed
  6. customThe aqueous phase was collected
  7. additiondiluted with ethanol and (prop-2-en-1-yl) bromide (8 ml)
  8. additionadded
  9. waitbeing continued overnight
  10. concentrationAfter concentration under vacuo the residue
  11. customwas partitioned between water and ethyl acetate
  12. customThe organic phase was collected
  13. dry with materialdried, over magnesium sulfate
  14. filtrationfiltered
  15. customthe solvent evaporated under reduced pressure

Sources & evidence

ORD record
ord-1ac1928fac3c428291f5e93e3fd7cd15
Source dataset
uspto-grants-1999_07
Patent number
US05929072

Reaction notes

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