5-(N,N-bis(2-chloroethyl)amino)-2,4-dinitrobenzamide → 5-[N,N-bis(2-chloroethyl)amino]-2,4-dinitrobenzonitrile
Reaction equation
[Cl:1][CH2:2][CH2:3][N:4]([C:8]1[C:9]([N+:20]([O-:22])=[O:21])=[CH:10][C:11]([N+:17]([O-:19])=[O:18])=[C:12]([CH:16]=1)[C:13]([NH2:15])=O)[CH2:5][CH2:6][Cl:7]>O=S(Cl)Cl.N#N>[Cl:1][CH2:2][CH2:3][N:4]([C:8]1[C:9]([N+:20]([O-:22])=[O:21])=[CH:10][C:11]([N+:17]([O-:19])=[O:18])=[C:12]([CH:16]=1)[C:13]#[N:15])[CH2:5][CH2:6][Cl:7]Participants
4
Reactant 1
Product 1
Reagents, catalysts & solvents 2
Procedure
A solution of 5-[N,N-bis(2-chloroethyl)amino]-2,4-dinitrobenzamide (1) (VII) (0.20 g, 0.57 mol) in SOCl2 (5 mL) was heated under reflux in N2 for 84 h. Excess SOCl2 was removed under reduced pressure, and the residue was chromatographed on silica gel. Elution with EtOAc/petroleum ether (3:7) gave 5-[N,N-bis(2-chloroethyl)amino]-2,4-dinitrobenzonitrile (7) (Ic: X=Cl, R=CN) (0.16 g, 87%), mp (CHCl3) 127° C. 1H NMR (CD3COCD3) δ 8.79 (s, 1 H, H-3), 8.19 (s, 1 H, H-6), 3.93 (s, 8 H, NCH2CH2Cl). 13C NMR δ 148.55 (C-5), 140.98, 139.07 (C-2,4), 129.50, 126.10 (C-3,6), 115.05 (C-1), 112.84 (CN), 54.18 (CH2N), 42.20 (CH2Cl). Anal. (C11H10Cl2N4O4) C,H,N.