Ethyl isocyanate → HCID 59603111, compound
Reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[N:10]=[C:9]([NH2:11])[S:8][C:5]2=[N:6][CH:7]=1.[CH2:12]([N:14]=[C:15]=[O:16])[CH3:13]>O1CCOCC1>[Br:1][C:2]1[CH:3]=[C:4]2[N:10]=[C:9]([NH:11][C:15]([NH:14][CH2:12][CH3:13])=[O:16])[S:8][C:5]2=[N:6][CH:7]=1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 80 °C
Procedure
To a solution of 6-bromothiazolo[5,4-b]pyridin-2-amine IV (1.30 g, 5.55 mmol) in 1,4-dioxane (20.0 mL) was added ethylisocyanate (2.19 mL, 27.07 mmol) and the resulting reaction mixture was heated to 80° C. for 8 h. After the completion of the reaction (TLC monitoring), 1,4-dioxane was distilled off followed by co-distillation with n-hexane (2 times). The residue was then stirred with water at 90° C. for 2 h followed by filtration to obtain the desired product that was further washed with hot water and then dried. The residue was finally washed with ether to obtain the desired product (1.40 g, 83%). 1H NMR (400 MHz, DMSO-d6): δ 1.10 (t, J=7.20 Hz, 3H), 3.20 (quintet, J=7.20 Hz, 2H), 6.76 (br s, 1H), 8.24 (d, J=2.0 Hz, 1H), 8.45 (d, J=2.0 Hz, 1H) and 11.05 (br s, 1H).