Hydrochloric Acid → N1-(4-methoxybenzoyl)-N2-(2-naphthoyl)-benzenediamine

HRID 427551Notes

Reaction equation

HRID 427551 reaction equation
[CH3:1][O:2][C:3]1[CH:18]=[CH:17][C:6]([C:7]([NH:9][C:10]2[C:11]([NH2:16])=[CH:12][CH:13]=[CH:14][CH:15]=2)=[O:8])=[CH:5][CH:4]=1.N1C=CC=CC=1.[CH:25]1[C:34]2[C:29](=[CH:30][CH:31]=[CH:32][CH:33]=2)[CH:28]=[CH:27][C:26]=1[C:35](Cl)=[O:36].Cl>C(Cl)(Cl)Cl.C(OCC)(=O)C>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([C:7]([NH:9][C:10]2[C:11]([NH:16][C:35]([C:26]3[CH:27]=[CH:28][C:29]4[C:34](=[CH:33][CH:32]=[CH:31][CH:30]=4)[CH:25]=3)=[O:36])=[CH:12][CH:13]=[CH:14][CH:15]=2)=[O:8])=[CH:17][CH:18]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 1049PyridineHCID 752462-Naphthoyl chlorideHCID 785232N-(2-Aminophenyl)-4-methoxybenzamide

Product 1

HCID 21352792N1-(4-methoxybenzoyl)-N2-(2-naphthoyl)-benzenediamineYield 65%

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of N1-(4-methoxybenzoyl)-1,2-benzenediamine (200 mg, 0.826 mmol) and pyridine (0.25 mL) in chloroform (5 mL) was treated with 2-naphthoyl chloride (158 mg, 0.826 mmol). After 20 h, the mixture was poured into a mixture of ethyl acetate and 1 N aqueous hydrochloric acid. The organic layer was washed with water, saturated sodium chloride solution, and dried (potassium carbonate), filtered, and concentrated in vacuo. Recrystallization from hexanes/ethyl acetate yielded 211 mg (65%) of the title compound.

Workup

  1. washThe organic layer was washed with water, saturated sodium chloride solution
  2. dry with materialdried (potassium carbonate)
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customRecrystallization from hexanes/ethyl acetate

Sources & evidence

ORD record
ord-e57c3078b0fb4425aebd02eed4b40bff
Source dataset
uspto-grants-2001_11
Patent number
US06313122B1

Reaction notes

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