Isoamyl Nitrite → Benzothiazolone
Reaction equation
N1(C(C[N:10]2[C:14]3[CH:15]=[CH:16][CH:17]=[CH:18][C:13]=3[S:12][C:11]2=[O:19])=O)CCNCC1.N(OCCC(C)C)=O>C(Cl)(Cl)Cl>[S:12]1[C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=2[NH:10][C:11]1=[O:19]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
To a solution of 3-[(1-piperazinyl)carbonylmethyl]-2-benzothiazolinone (3.0 g) in chloroform (50 ml) was added dropwise isoamyl nitrite (7.3 ml), for a period of 10 minutes below 20° C. The mixture was stirred for 18 hours at ambient temperature. Then, the reaction mixture was extracted with chloroform. The extract was washed with water, dried over magnesium sulfate and evaporated to give a crystalline product, which was recrystallized from a mixture of ethyl acetate and ethanol to give 3-[4-nitroso-1-piperazinyl)carbonylmethyl]-2-benzothiazolinone (2.54 g) as needles.