Reaktion #833976

Reaktionsgleichung

NH4Cl

2-(4-Bromo-phenyl)-thiophene-3-ylamine

DBU

propane-2-sulfonyl chloride

→

propane-2-sulfonic acid[2-(4-bromo-phenyl)-thiophene-3-yl]-amide

Lösungsmittel

CH2Cl2

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.ADDITIONCharge a double jacketed 20 L reactor
2. 2
   Sonstigeequipped with mechanical stirrer
3. 3
   SonstigeObtain a clear solution
4. 4
   SonstigeAfter completion of reaction
5. 5
   Temperaturcool the reaction mixture to 11° C.
6. 6
   workup.ADDITIONadd an aqueous solution of satd
7. 7
   TemperaturHeat the mixture to 20° C.
8. 8
   Sonstigeseparate the aqueous phase
9. 9
   WaschenWash the organic layer with 2N HCl (5.12 L)
10. 10
    Sonstigeevaporate to dryness
11. 11
    TemperaturHeat the mixture
12. 12
    workup.DISSOLUTIONuntil complete dissolution at 70° C
13. 13
    TemperaturCool the solution to 41° C.
14. 14
    workup.ADDITIONadd water (1384 mL)
15. 15
    workup.STIRRINGStir the suspension overnight at 22° C.
16. 16
    Filtrationfilter
17. 17
    Waschenwash two times with 254 mL of a 1/1 EtOH/H2O mixture
18. 18
    SonstigeDry the resulting beige solid under vacuum at 26° C. for 4 days

Vorschrift

Charge a double jacketed 20 L reactor equipped with mechanical stirrer and set under inert atmosphere of argon with 2-(4-Bromo-phenyl)-thiophene-3-ylamine (562 g, 2.21 mol) and CH2Cl2 (9.435 L). Obtain a clear solution. Add DBU (1.999 L) and cool the mixture to 9.4° C. Add propane-2-sulfonyl chloride (0.616 g) in 20 minutes maintaining the temperature below 25° C. Stir the reaction mixture 22 h at 20° C. After completion of reaction, cool the reaction mixture to 11° C. and add an aqueous solution of satd. aq. NH4Cl (7.65 L) cooled at 10° C. in 5 minutes. Heat the mixture to 20° C. and separate the aqueous phase. Wash the organic layer with 2N HCl (5.12 L), evaporate to dryness and take the residue into ethyl alcohol (800 g) . Heat the mixture until complete dissolution at 70° C. Cool the solution to 41° C. and add water (1384 mL). Stir the suspension overnight at 22° C., filter and wash two times with 254 mL of a 1/1 EtOH/H2O mixture. Dry the resulting beige solid under vacuum at 26° C. for 4 days to give propane-2-sulfonic acid[2-(4-bromo-phenyl)-thiophene-3-yl]-amide (688 g, 1.9 mol). 1H NMR (250 MHz, CDCl3): 1.25(d,6 H, J=6.9 H), 3.16 (hept, 1 H, J=6.9 Hz), 7.28(pseudo s, 2 H), 7.33(d, 2 H, J=8.5 Hz), 7.6(d, 2 H, J=8.5 Hz)

Quelle