5-(N,N-bis(2-chloroethyl)amino)-2,4-dinitrobenzamide → 5-[N,N-bis(2-chloroethyl)amino]-2,4-dinitrobenzonitrile

HRID 1899057Notes

Reaction equation

HRID 1899057 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

HCID 1266905-(N,N-bis(2-chloroethyl)amino)-2,4-dinitrobenzamide

Product 1

HCID 3725665-[N,N-bis(2-chloroethyl)amino]-2,4-dinitrobenzonitrileYield 87%

Reagents, catalysts & solvents 2

HCID 947NitrogenSolventHCID 24386Thionyl ChlorideSolvent

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.

Workup

  1. customExcess SOCl2 was removed under reduced pressure
  2. customthe residue was chromatographed on silica gel
  3. washElution with EtOAc/petroleum ether (3:7)

Sources & evidence

ORD record
ord-3814befa580844bcafae13b0fa2e7feb
Source dataset
uspto-grants-1996_11
Patent number
US05571845

Reaction notes

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