Isobutylamine → 3,5-bisnitro-N-(2-methylpropyl)benzamide

HRID 2259269Notes

Reaction equation

HRID 2259269 reaction equation
[CH2:1]([NH2:5])[CH:2]([CH3:4])[CH3:3].[N+:6]([C:9]1[CH:10]=[C:11]([CH:15]=[C:16]([N+:18]([O-:20])=[O:19])[CH:17]=1)[C:12](Cl)=[O:13])([O-:8])=[O:7]>C(OCC)(=O)C>[CH2:1]([NH:5][C:12](=[O:13])[C:11]1[CH:10]=[C:9]([N+:6]([O-:8])=[O:7])[CH:17]=[C:16]([N+:18]([O-:20])=[O:19])[CH:15]=1)[CH:2]([CH3:4])[CH3:3]

Participants

4

Reactant 2

HCID 6558IsobutylamineHCID 74323,5-Dinitrobenzoyl chloride

Product 1

HCID 31133543,5-bisnitro-N-(2-methylpropyl)benzamideYield 27.2%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

The general procedure was used with isobutyl amine (14.6 g, 0.200 mole) and 3,5-dinitrobenzoyl chloride (23.0 g, 0.100 mole) in ethyl acetate. Produced 7.28 g (26%) crystals, mp 149°-155° C. Proton NMR (90 MHz) shows resonances at 9.168 ppm (m, 1H; 4-aryl H); 8.955 ppm (d, 2 Hz, 2H; 2,6-aryl H's); 6.526 ppm (bs, 1H; N-H); 3.378 ppm (t, 6.4 Hz, 2H; N-CH2); 2.050 ppm (sep, 7 Hz, 1H; CH); 1.021 ppm (d, 6.2 Hz, 6H; CH3).

Sources & evidence

ORD record
ord-b9be7aa7dfbd49fba64f4fbd46d7c159
Source dataset
uspto-grants-1995_12
Patent number
US05472983

Reaction notes

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