2-chloro-3,5-dinitrobenzamide → 3,5-Dinitrobenzamide

HRID 1058513Notes

Reaction equation

HRID 1058513 reaction equation
Cl[C:2]1[C:10]([N+:11]([O-:13])=[O:12])=[CH:9][C:8]([N+:14]([O-:16])=[O:15])=[CH:7][C:3]=1[C:4]([NH2:6])=[O:5]>C(OCC)(=O)C>[N+:11]([C:10]1[CH:2]=[C:3]([CH:7]=[C:8]([N+:14]([O-:16])=[O:15])[CH:9]=1)[C:4]([NH2:6])=[O:5])([O-:13])=[O:12]

Participants

3

Reactant 1

HCID 2356272-chloro-3,5-dinitrobenzamide

Product 1

HCID 45113,5-Dinitrobenzamide

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

Preparation of 2-(aziridin-1-yl)-3,5-dinitrobenzamide(14) Reaction of 2-chloro-3,5-dinitrobenzamide [Palmer et al., J.Med.Chem. 1996, 39, 2518-2528] in ethyl acetate as described in Example C except that the reaction time was 2 hours, gave 2-aziridin-1-yl)-3,5-dinitrobenzamide (14) as a yellow powder, mp 200° C. [Kahn & Ross, Chem-Biol. Int., 1969-70,1, 27-47, record mp 196° C.]1H NMR [CD3)2SO] δ8 74 (d, J=2.6 Hz, 1H, H-4), 8.35(d,J=2 Hz, 1H, H-6), 8.10, 7 93 (2 br s,2H, CONH2), 2.40 (s, 4H, aziridine-H) 13NMR δ

Sources & evidence

ORD record
ord-9639af63cf6c425cbc440b17d18107a9
Source dataset
uspto-grants-2003_02
Patent number
US06517836B1

Reaction notes

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