Acetonitrile → 3,5-Dinitrobenzamide

HRID 1650333Notes

Reaction equation

HRID 1650333 reaction equation
C([O-])(O)=O.[Na+].C(#[N:8])C.[N+:9]([C:12]1[CH:13]=[C:14]([CH:18]=[C:19]([N+:21]([O-:23])=[O:22])[CH:20]=1)[C:15](Cl)=[O:16])([O-:11])=[O:10]>O>[N+:9]([C:12]1[CH:13]=[C:14]([CH:18]=[C:19]([N+:21]([O-:23])=[O:22])[CH:20]=1)[C:15]([NH2:8])=[O:16])([O-:11])=[O:10]

Participants

5

Reactant 3

HCID 6342AcetonitrileHCID 74323,5-Dinitrobenzoyl chlorideHCID 516892Sodium Bicarbonate

Product 1

HCID 45113,5-Dinitrobenzamide

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

The L-malic salt (5 mg, 14 μm) was dissolved in a mixture of 1 ml H2O, 3.5 mg (3 meq) NaHCO3, and 1 ml acetonitrile and 3.2 mg (14 μm) of 3,5-dinitrobenzoyl chloride was added and the reaction stirred for 16 hr at room temperature. After 5 ml H2O was added, the reaction was vacuum filtered and washed with H2O (2×1 ml portions), cold isopropanol (2×1 ml portions) and diethyl ether (2×2 ml) to isolate 2.5 mg of the 3,5-dinitrobenzamide, "DBN", (85 area % by gradient reverse phase HPLC).

Workup

  1. additionwas added
  2. filtrationfiltered
  3. washwashed with H2O (2×1 ml portions), cold isopropanol (2×1 ml portions) and diethyl ether (2×2 ml)

Sources & evidence

ORD record
ord-28dd310de65d4275bf80288dfa3edeae
Source dataset
uspto-grants-1990_05
Patent number
US04923983

Reaction notes

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