تفاعل #1521834

معادلة التفاعل

pyridine

(8-Trifluoromethylquinolin-4-yloxy)-acetic acid

oxalyl chloride

N′-(2-thiazolyl)sulfanilamide

→

solid

المردود 69.5%

N-[4-(Thiazol-2-ylsulfamoyl)-phenyl]-2-(8-trifluoromethyl-quinolin-4-yloxy)-acetamide

المردود 69.5%

المذيبات

DCM

ظروف التفاعل

المعالجة

1. 1
   أخرىSolvent and excess oxalyl chloride were removed in vacuo
2. 2
   درجة الحرارةto warm to rt overnight
3. 3
   أخرىThe solid was collected
4. 4
   غسيلrinsed with fresh DCM
5. 5
   أخرىFurther purification
6. 6
   workup.STIRRINGstirring vigorously for 4 h
7. 7
   ترشيحfiltration
8. 8
   أخرىAfter drying under vacuum

الإجراء التجريبي

(8-Trifluoromethylquinolin-4-yloxy)-acetic acid (0.50 g, 1.84 mmol) was suspended in 20 mL DCM with rapid stirring. At rt, oxalyl chloride (0.19 mL, 1.2 equiv) was added dropwise and stirring continued for 4 h. Solvent and excess oxalyl chloride were removed in vacuo, the white residue was re-suspended in DCM, and the mixture cooled to 0° C. N′-(2-thiazolyl)sulfanilamide (0.47 g, 1.0 equiv) was added followed by pyridine (0.30 mL, 2.0 equiv). The mixture was allowed to warm to rt overnight. The solid was collected and rinsed with fresh DCM. Further purification was effected by suspending the solid in 20 mL methanol, stirring vigorously for 4 h, and filtration. After drying under vacuum, white solid 0.65 g (69%) was obtained. 1H-NMR (DMSO-d6) 5.11 (s, 2H), 6.79 (d, J=4.8 Hz, 1H), 7.12 (d, J=5.2 Hz, 1H), 7.22 (d, J=4.8 Hz, 1H), 7.71 (t, J=8.0 Hz, 1H), 8.17 (d, J=8.0 Hz, 1H), 8.55 (d, J=8.0 Hz, 1H), 8.85 (d, J=5.2 Hz, 1H),; 13C-NMR (DMSO-d6) 68.0, 103.6, 108.8, 120.0, 122.0, 124.8 (q, J=270 Hz), 125.1, 125.4, 126.4 (q, J=33 Hz), 127.7, 127.8, 129.2, 137.7, 142.1, 145.6, 153.2, 161.2, 166.5, 169.4 LC/MS (10-99%) M/Z: M+1 obs=509.5; tR=3.13 min.

المصدر