4-Chlorobenzoyl chloride → N1-(4-tert-Butylbenzoyl)-N2-(4-chlorobenzoyl)-1,2-benzenediamine

HRID 395846Notes

Reaction equation

HRID 395846 reaction equation
[C:1]([C:5]1[CH:20]=[CH:19][C:8]([C:9]([NH:11][C:12]2[C:13]([NH2:18])=[CH:14][CH:15]=[CH:16][CH:17]=2)=[O:10])=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2].[Cl:21][C:22]1[CH:30]=[CH:29][C:25]([C:26](Cl)=[O:27])=[CH:24][CH:23]=1.C(=O)([O-])[O-].[K+].[K+].[OH-].[Na+]>C(Cl)Cl.CCOCC.O1CCCC1>[C:1]([C:5]1[CH:20]=[CH:19][C:8]([C:9]([NH:11][C:12]2[C:13]([NH:18][C:26](=[O:27])[C:25]3[CH:29]=[CH:30][C:22]([Cl:21])=[CH:23][CH:24]=3)=[CH:14][CH:15]=[CH:16][CH:17]=2)=[O:10])=[CH:7][CH:6]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

8

Reactant 4

HCID 85014-Chlorobenzoyl chlorideHCID 11430Potassium CarbonateHCID 14798Sodium HydroxideHCID 1133079N-(2-aminophenyl)-4-tert-butylbenzamide

Product 1

HCID 10525429N1-(4-tert-Butylbenzoyl)-N2-(4-chlorobenzoyl)-1,2-benzenediamineYield 66.4%

Reagents, catalysts & solvents 3

HCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of N1-(4-tert-butylbenzoyl)-1,2-benzenediamine (100 mg, 0.37 mmol) in 3 mL methylene chloride was added 4-chlorobenzoyl chloride (95 μL, 0.74 mmol) and excess potassium carbonate. The mixture was stirred 30 min then a 1:1 solution of tetrahydrofuran and 5 N NaOH was added. The resultant mixture was stirred an additional 20 min and diluted with ether. The mixture was washed twice with water, dried over magnesium sulfate, filtered and concentrated in vacuo. The residue was sonicated with hexane causing a precipitate to form which was collected by filtration and dried under vacuum to yield 100 mg (66%) of the title compound.

Workup

  1. washThe mixture was washed twice with water
  2. dry with materialdried over magnesium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customThe residue was sonicated with hexane causing a precipitate
  6. customto form which
  7. filtrationwas collected by filtration
  8. customdried under vacuum

Sources & evidence

ORD record
ord-e20abf1e59e74181adf8ecdcdeb225ca
Source dataset
uspto-grants-2003_08
Patent number
US06605626B2

Reaction notes

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