Acetone → 2,5-Dicarbamoylbenzoic acid

HRID 1457543Notes

Reaction equation

HRID 1457543 reaction equation
[C:1]([C:4]1[CH:5]=[C:6]2[C:11](=[O:12])[NH:10][C:8](=[O:9])[C:7]2=[CH:13][CH:14]=1)(=[O:3])[NH2:2].C(Cl)(=O)C1C(=CC(=CC=1)C(Cl)=O)C(Cl)=[O:19].N.CC(C)=[O:33]>C(OCC)(=O)C.C(Cl)(Cl)Cl.ClCCl>[C:11]([C:6]1[CH:5]=[C:4]([C:1](=[O:3])[NH2:2])[CH:14]=[CH:13][C:7]=1[C:8]([OH:19])=[O:9])(=[O:12])[NH2:10].[C:8]([C:7]1[CH:13]=[CH:14][C:4]([C:1](=[O:3])[NH2:2])=[CH:5][C:6]=1[C:11]([OH:33])=[O:12])(=[O:9])[NH2:10]

Participants

9

Reactant 4

HCID 180AcetoneHCID 222Ammonia2×HCID 774721,2,4-Benzenetricarbonyl trichloride2×HCID 106792194-Carbamoylphthalimide

Product 2

HCID 198051532,5-Dicarbamoylbenzoic acidHCID 220044202,4-Dicarbamoylbenzoic acid

Reagents, catalysts & solvents 3

HCID 6212ChloroformSolventHCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

In this step, 4-carbamoylphthalimide is prepared by reacting trimellitoyl chloride with ammonia and dehydrating the obtained product. Specifically, this reaction is conducted by reacting trimellitoyl chloride with aqueous ammonia either without any solvent or in a state dissolved in a solvent at a temperature ranging from about -15° C. to room temperature. The solvent to be used in this case is preferably acetone, dichloromethane, chloroform or ethyl acetate, though any organic solvent inert to the reaction may be used. The resulting reaction mixture is treated with an acid to give a mixture comprising 2,4-dicarbamoylbenzoic acid and 2,5-dicarbamoylbenzoic acid. This mixture is further treated in the absence or presence of a solvent for 0.5 to 24 hours to give the objective compound. This treatment is conducted at room temperature to about 200° C. The solvent to be used in this treatment is preferably N-methyl-2-pyrrolidinone, though any solvent inert to the reaction may be used.

Workup

  1. dissolutionwithout any solvent or in a state dissolved in a solvent at a temperature
  2. customranging from about -15° C. to room temperature
  3. customthough any organic solvent inert to the reaction
  4. customThe resulting reaction mixture
  5. additionis treated with an acid

Sources & evidence

ORD record
ord-62593eaf880d44f2b3ab2f007028e3a0
Source dataset
uspto-grants-1998_12
Patent number
US05849741

Reaction notes

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