تفاعل #1492129

معادلة التفاعل

NaH

Crude compound 72

Benzo[b]thiophene-2-thiol

THF

2-chloro-1-(3,4-dihydroquinolin-1(2H)-yl)ethanone

THF

→

compound 5

1,2,3,4-tetrahydro-benzo[b]azepin-5-one

ظروف التفاعل

المعالجة

1. 1
   درجة الحرارةcooled down to 0° C
2. 2
   workup.STIRRINGThe formed suspension was stirred for 40 min at 0° C.
3. 3
   workup.STIRRINGThe reaction mixture was stirred at RT for 16 h

الإجراء التجريبي

Crude compound 72 (0.71 g, 4.3 mmol) was dissolved in 40 mL of dry THF under N2, stirred for 30 min at RT and then cooled down to 0° C. NaH (60% in mineral oil, 0.224 g, 5.5 mmol) was added to the ice-cold solution which became a yellowish suspension. The formed suspension was stirred for 40 min at 0° C. and then 2-chloro-1-(3,4-dihydroquinolin-1(2H)-yl)ethanone (0.89 g, 4.3 mmol) was added as a solution in 4 mL of dry THF. The reaction mixture was stirred at RT for 16 h. The work-up, the same as for compound 5, gave crude material which was purified by flash chromatography (CH2Cl2/EtOAc) giving 0.56 g of the crude product. Pumping the crude product under high vacuum over P4O10 at 45° C. for 4 h removed the co-crystallized EtOAc to yield the desired product 73 (36%): MS: m/z+ 340.1 [M+H]+; Anal. Calcd (found) for C19H17NOS2: C, 67.22 (67.18); H, 5.05 (5.11); N, 4.13 (4.08); S, 18.89 (18.70).

المصدر