Ammonia → 4-Methyl-3,5-dinitrobenzamide

HRID 968783Notes

Reaction equation

HRID 968783 reaction equation
[CH3:1][C:2]1[C:10]([N+:11]([O-:13])=[O:12])=[CH:9][C:5]([C:6](O)=[O:7])=[CH:4][C:3]=1[N+:14]([O-:16])=[O:15].C([N:19](CC)CC)C.COC(Cl)=O.N>C(#N)C>[CH3:1][C:2]1[C:10]([N+:11]([O-:13])=[O:12])=[CH:9][C:5]([C:6]([NH2:19])=[O:7])=[CH:4][C:3]=1[N+:14]([O-:16])=[O:15]

Participants

6

Reactant 4

HCID 222AmmoniaHCID 6586Methyl chloroformateHCID 8471TriethylamineHCID 854773,5-Dinitro-p-toluic acid

Product 1

HCID 33186984-Methyl-3,5-dinitrobenzamideYield 91.1%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent2×

Procedure

To a suspension of 4-methyl-3,5-dinitrobenzoic acid (3) (1.5 g) in acetonitrile (22.5 g, 30 mL) and triethylamine (0.87 g, 1.2 mL) at −10° C. is slowly added a solution of methylchloroformate (0.723 g, 0.6 m-L) in acetonitrile (2.25 g, 3 mL). The resulting mixture is agitated at −10° C. for about 1 hour, whereupon ammonia gas (excess) is bubbled though the mixture for about 30 minutes. The resultant mixture is allowed to age at about −5 to −10° C. for 12 hours, whereupon the mixture is added to a mixture of ice and water (100 mL). The solid that precipitates is filtered and dried to provide 4-methyl-3,5-dinitrobenzamide (6) (1.36 g, 91% Yield).

Workup

  1. customis bubbled though the mixture for about 30 minutes
  2. additionis added to a mixture of ice and water (100 mL)
  3. customThe solid that precipitates
  4. filtrationis filtered
  5. customdried

Sources & evidence

ORD record
ord-041a23abff4645019b7802b356d36475
Source dataset
uspto-grants-2007_12
Patent number
US07304084B2

Reaction notes

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