N,N-Dimethylcyclohexylamine → 6-chloro-N-(3-methylbutan-2-yl)-1,1-dioxo-4H-thieno[3,2-e][1,2,4]thiadiazin-3-amine

温度

200 °C

Phosphorus pentoxide (2.84 g; 20 mmol), N,N-dimethylcyclohexylamine (5 ml, 33 mmol) and 1,2-dimethylpropylamine hydrochloride (2.47 g; 20 mmol) were carefully mixed in a three necked flask equipped with mechanical stirring and condenser with drying tube. The mixture was heated on an oil bath at 200° C. until a homogeneous mass was obtained. Then 6-chloro-2,3-dihydro-3-oxo-4H-thieno[3,2-e]-1,2,4-thiadiazine 1,1-dioxide (1.2 g; 5 mmol) was added and the mixture was stirred at 240° C. for 45 min. The mixture was allowed to cool to about 100° C., 150 ml of water was added and stirring was continued at ambient temperature for approximately 1 h. The hydrolysed mixture was filtered and the dark precipitate was washed with water and dissolved in boiling ethanol, treated with charcoal, filtered and finally evaporated to dryness. Flash chromatography (ethyl acetate/silica gel) afforded 105 mg (7%) of the pure title compound; m.p. 216°-218° C.; 1H-NMR (DMSO-d6): δ 0.90 (d, 6H, CH(CH3)2), 1.08 (d, 3H, NCHCH3), 1.75 (m, 1H, CH(CH3)2), 3.65 (m, 1H, NHCH), 7.11 (br. s, 2H, 5-H+NH), 10.68 (s, 1H, NH); MS m/e: 307/309 (M+).

1. customequipped
2. customcondenser with drying tube
3. customwas obtained
4. stirringthe mixture was stirred at 240° C. for 45 min
5. temperatureto cool to about 100° C.
6. stirringstirring
7. filtrationThe hydrolysed mixture was filtered
8. washthe dark precipitate was washed with water
9. dissolutiondissolved
10. additiontreated with charcoal
11. filtrationfiltered
12. customfinally evaporated to dryness

ORDレコード

ord-7a6d6969eb934f178aac4cdfdb5bad94

出典データセット

uspto-grants-1999_03

DOI

10.6084/m9.figshare.5104873.v1

特許番号

US05889002