Ammonia → 2,5-Dicarbamoylbenzoic acid

HRID 324339Notes

Reaction equation

HRID 324339 reaction equation
C(Cl)(=O)C1C(=CC(=CC=1)C(Cl)=O)C(Cl)=[O:5].[NH3:16].Cl.[C:18]([C:21]1[CH:29]=[C:28]([C:30](=[O:32])[NH2:31])[CH:27]=[CH:26][C:22]=1[C:23]([OH:25])=O)(=[O:20])N>CC(C)=O>[C:23]([C:22]1[CH:26]=[CH:27][C:28]([C:30](=[O:32])[NH2:31])=[CH:29][C:21]=1[C:18]([OH:20])=[O:5])(=[O:25])[NH2:16]

Participants

6

Reactant 4

HCID 222Ammonia2×HCID 313Hydrochloric AcidHCID 774721,2,4-Benzenetricarbonyl trichlorideHCID 220044202,4-Dicarbamoylbenzoic acid

Product 1

HCID 198051532,5-Dicarbamoylbenzoic acidYield 89%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A solution of 21.1 g (0.10 mol) of trimellitoyl chloride in 25 ml of acetone was dropped into 200 ml of 29% aqueous ammonia, while the aqueous ammonia was stirred under cooling with ice. The resulting mixture was as such stirred for one hour, deaerated in a vacuum and acidified with concentrated hydrochloric acid under cooling with ice. The crystals thus precipitated were recovered by filtration, washed with water and dried with hot air to give 18.5 g of a mixture of 2,4-dicarbamoylbenzoic acid and 2,5-dicarbamoylbenzoic acid as a white crystal (yield: 89%).

Workup

  1. temperatureunder cooling with ice
  2. stirringas such stirred for one hour
  3. temperatureunder cooling with ice
  4. customThe crystals thus precipitated
  5. filtrationwere recovered by filtration
  6. washwashed with water
  7. customdried with hot air

Sources & evidence

ORD record
ord-0fe0adb2e7a6435d80fe08fd219c4e41
Source dataset
uspto-grants-2001_04
Patent number
US06218392B1

Reaction notes

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