Ammonia → 2,5-Dicarbamoylbenzoic acid

HRID 1457544Notes

Reaction equation

HRID 1457544 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-2e4a395faf9b45ae99017e37e02c8394
Source dataset
uspto-grants-1998_12
Patent number
US05849741

Reaction notes

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