تفاعل #2460295

معادلة التفاعل

Methanol

2-[(3-methoxyphenyl)thio]diethylbenzamide

lithium diisopropylamide

→

1-methoxythioxanthen-9-one

المذيبات

tetrahydrofuran

tetrahydrofuran

heptane THF

ظروف التفاعل

المعالجة

1. 1
   درجة الحرارةThe reaction mixture was warmed to ambient and
2. 2
   غسيلthe resulting solution was washed twice with water
3. 3
   تجفيفThe solution was dried (Na2SO4)
4. 4
   أخرىthe solvent was removed at reduced pressure
5. 5
   أخرىThis crude product was recrystallized from methanol
6. 6
   أخرىto provide 0.15 g (45% of theory) of a yellow solid

الإجراء التجريبي

Finally, 1-methoxythioxanthen-9-one (S-12) was prepared. A stirred mixture of 2.05 mL of a 2.0 M solution in heptane/THF of lithium diisopropylamide (4.1 mmol) diluted with 15 mL of anhydrous tetrahydrofuran was cooled to 0° C. and treated dropwise with a solution of 2-[(3-methoxyphenyl)thio]diethylbenzamide (0.4 g, 1.4 mmol) in 3 mL of anhydrous tetrahydrofuran. The reaction mixture was warmed to ambient and stirred for 2 h. Methanol (1 mL) was added, and the resulting solution was washed twice with water, and then with brine. The solution was dried (Na2SO4) and the solvent was removed at reduced pressure to deposit a yellow solid. This crude product was recrystallized from methanol to provide 0.15 g (45% of theory) of a yellow solid. 1H NMR (CDCl3): δ 4.00 (s, 3H), 7.92 (d, 1H), 7.12 (d, 1H), 7.50 (m, 4H), 8.45 (d, 1H).

المصدر