Reaktion #215758

Reaktionsgleichung

2-methyl bromopropane

Sodium hydride

product

4-Methyl-2H-thieno[3,2-e]-1,2,3-thiadiazine-6-sulfonamide 1,1-dioxide

→

desired compound

Ausbeute 56.2%

4-Methyl-2-(2-methylpropyl)-2H-thieno[3,2-e]-1,2,3-thiadiazine-6-sulfonamide 1,1-dioxide

Ausbeute 56.2%

Lösungsmittel

water

DMF

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.STIRRINGstirred for 2h
2. 2
   TemperaturAnd then cooled to 0° C.
3. 3
   workup.STIRRINGstirred for 12h
4. 4
   SonstigeDMF was evaporated under high vacuum
5. 5
   SonstigeThe residue obtained
6. 6
   Extraktionextracted with ethyl acetate (3×20 mL)
7. 7
   TrocknenThe combined extracts were dried over MgSO4
8. 8
   Sonstigeevaporated
9. 9
   Sonstigeto provide an oil which
10. 10
    Sonstigewas purified by flash column chromatography (silica, hexane-ethyl acetate gradient)

Vorschrift

The product from step B (0.9 g, 2.85 mmol) was dissolved in DMF (10 mL). Sodium hydride (0.17 g, 4.28 mmol of a 60% suspension in mineral oil) was added slowly at room temperature. The mixture was stirred for 15 min and then 2-methyl bromopropane (0.47 mL, 4.28 mmol) was added. The mixture was warmed to 80° C. and stirred for 2h. And then cooled to 0° C. and stirred for 12h. DMF was evaporated under high vacuum. The residue obtained was diluted with water (20 mL) and extracted with ethyl acetate (3×20 mL). The combined extracts were dried over MgSO4 and evaporated to provide an oil which was purified by flash column chromatography (silica, hexane-ethyl acetate gradient) to give the desired compound as a white solid (0.54 g, 50%). mp: 140°-142° C. 1H NMR (DMSO-d6): δ:0.89 (6H, d, 2CH3); 2.03 (1H, m, CH); 2.49 (3H, s, CH3); 3.64 (2H, δ, CH2); 7.94 (1H, s, CH); 8.21 (2H, s, NH2 exchangeable). Analysis calculated for C9H13N3O4S3 : C, 35.59; H, 4.78; N, 12.45 Found: C, 35.56; H, 4.44; N, 12.36.

Quelle