Reaktion #74560

Reaktionsgleichung

HCl

3-cyano-4-fluorobenzenesulfonyl chloride

2-aminothiazole

pyridine

→

title product

Ausbeute 66.6%

3-cyano-4-fluoro-N-(thiazol-2-yl)benzenesulfonamide

Ausbeute 66.6%

Lösungsmittel

dichloromethane

dichloromethane

Reaktionsbedingungen

Aufarbeitung

1. 1
   Sonstigeto give a solution
2. 2
   workup.STIRRINGThe reaction was stirred at this temperature for 2 days
3. 3
   Sonstigebefore decanting the supernatant and
4. 4
   Einengenconcentrating in vacuo
5. 5
   Sonstigeto furnish a dark oil
6. 6
   Sonstigethe mixture triturated until solidification
7. 7
   FiltrationA brick red solid was filtered off
8. 8
   Waschenwashed with water
9. 9
   Sonstigedried

Vorschrift

To 2-aminothiazole (12.55 g, 125.3 mmol) was added pyridine (46 ml) and dichloromethane (75 mL) and the mixture stirred to give a solution. A solution of 3-cyano-4-fluorobenzenesulfonyl chloride (25 g, 114 mmol) in dichloromethane (50 ml) was added over approx 20 minutes at room temperature. The reaction was stirred at this temperature for 2 days before decanting the supernatant and concentrating in vacuo to furnish a dark oil. 2M HCl (200 ml) was added and the mixture triturated until solidification occurred. A brick red solid was filtered off, washed with water and dried to furnish 21.5 g of the title product. 1HNMR (d6-DMSO): δ 6.9 (d, 1H), 7.3 (m, 1H), 7.6 (m, 1H), 8.15 (m, 1H), 8.3 (d, 1H), 12.9 (br s 1H). LCMS Rt=2.34 min MS m/z 284 [MH]+.

Quelle