تفاعل #2286344

معادلة التفاعل

(2-cyano-2-{[3,5-dichloro-4-(5-isopropyl-6-oxo-1,6-dihydro-pyridazin-3-ylsulfanyl)-phenyl]-hydrazono}-acetyl)-carbamic acid ethyl ester

(2-Cyano-2-{[3,5-dichloro-4-(5-isopropyl-6-oxo-1,6-dihydro-pyridazin-3-ylsulfanyl)-phenyl]-hydrazono}-acetyl)-carbamic acid ethyl ester

sodium acetate

→

2-[3,5-dichloro-4-(5-isopropyl-6-oxo-1,6-dihydro-pyridazin-3-ylsulfanyl)-phenyl]-3,5-dioxo-2,3,4,5-tetrahydro-[1,2,4]triazine-6-carbonitrile

المردود 103.2%

2-[3,5-Dichloro-4-(5-isopropyl-6-oxo-1,6-dihydro-pyridazin-3-ylsulfanyl)-phenyl]-3,5-dioxo-2,3,4,5-tetrahydro-[1,2,4]triazine-6-carbonitrile

المردود 103.2%

المذيبات

methylene chloride

acetic acid

ظروف التفاعل

المعالجة

1. 1
   أخرىconsumption of the starting material and conversion to product
2. 2
   درجة الحرارةThe reaction was cooled to 25° C.
3. 3
   workup.ADDITIONpoured onto water (200 mL)
4. 4
   استخلاصwas extracted with ethyl acetate (2×150 mL)
5. 5
   غسيلThe organics were washed with a saturated aqueous sodium chloride solution (1×150 mL)
6. 6
   تجفيفdried with magnesium sulfate
7. 7
   ترشيحfiltered
8. 8
   تركيزconcentrated under vacuum
9. 9
   أخرىto give an orange solid
10. 10
    تركيزhexanes mixture and concentrated in vacuo three times
11. 11
    workup.DISSOLUTIONIt was then dissolved in a 1:1 methylene chloride
12. 12
    تركيزmethanol mixture and concentrated under vacuum

الإجراء التجريبي

A solution of (2-cyano-2-{[3,5-dichloro-4-(5-isopropyl-6-oxo-1,6-dihydro-pyridazin-3-ylsulfanyl)-phenyl]-hydrazono}-acetyl)-carbamic acid ethyl ester (86) (2.98 g, 5.99 mmol) in glacial acetic acid (60 mL) was treated with sodium acetate (2.46 g, 29.95 mmol). The resulting mixture was heated to 120° C. for 3 h. At this time, LCMS indicated complete consumption of the starting material and conversion to product. The reaction was cooled to 25° C., poured onto water (200 mL) and was extracted with ethyl acetate (2×150 mL). The organics were washed with a saturated aqueous sodium chloride solution (1×150 mL), dried with magnesium sulfate, filtered and concentrated under vacuum to give an orange solid. This solid was dissolved in a 1:1 methylene chloride:hexanes mixture and concentrated in vacuo three times. It was then dissolved in a 1:1 methylene chloride: methanol mixture and concentrated under vacuum to afford 2-[3,5-dichloro-4-(5-isopropyl-6-oxo-1,6-dihydro-pyridazin-3-ylsulfanyl)-phenyl]-3,5-dioxo-2,3,4,5-tetrahydro-[1,2,4]triazine-6-carbonitrile (87) (2.79 g) as an orange solid. The material was used without further purification; ES(+)-HRMS m/e calcd for C17H12Cl2N6O3S (M+H)+ 451.0142, found 451.0143. Exact Mass=450.0069; Molecular weight=451.29

المصدر