Pyridine → N1-(4-methoxybenzoyl)-N2-(4-propylbenzoyl)-4-(tert-butyldimethylsilyloxy)-1,2-benzenediamine

HRID 427575

Reaction equation

HRID 427575 reaction equation
[CH3:1][O:2][C:3]1[CH:26]=[CH:25][C:6]([C:7]([NH:9][C:10]2[C:11]([NH2:24])=[CH:12][C:13]([O:16][Si:17]([C:20]([CH3:23])([CH3:22])[CH3:21])([CH3:19])[CH3:18])=[CH:14][CH:15]=2)=[O:8])=[CH:5][CH:4]=1.N1C=CC=CC=1.[CH2:33]([C:36]1[CH:44]=[CH:43][C:39]([C:40](Cl)=[O:41])=[CH:38][CH:37]=1)[CH2:34][CH3:35]>C(Cl)Cl>[CH3:1][O:2][C:3]1[CH:26]=[CH:25][C:6]([C:7]([NH:9][C:10]2[C:11]([NH:24][C:40](=[O:41])[C:39]3[CH:43]=[CH:44][C:36]([CH2:33][CH2:34][CH3:35])=[CH:37][CH:38]=3)=[CH:12][C:13]([O:16][Si:17]([C:20]([CH3:23])([CH3:21])[CH3:22])([CH3:19])[CH3:18])=[CH:14][CH:15]=2)=[O:8])=[CH:5][CH:4]=1

Participants

5

Reactant 3

HCID 1049PyridineHCID 1042934-Propylbenzoyl chlorideHCID 54024338N1-(4-methoxybenzoyl)-4-(tert-butyldimethylsilyloxy)-1,2-benzenediamine

Product 1

HCID 54350608N1-(4-methoxybenzoyl)-N2-(4-propylbenzoyl)-4-(tert-butyldimethylsilyloxy)-1,2-benzenediamine

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of N1-(4-methoxybenzoyl)-4-(tert-butyldimethylsilyloxy)-1,2-benzenediamine (300 mg, 0.81 mmol) in methylene chloride (20 mL) was added pyridine (0.13 mL, 1.6 mmol) followed by 4-propylbenzoyl chloride (0.15 mL, 0.89 mmol). The reaction mixture was stirred for 4 h, diluted with methylene chloride, washed with saturated aqueous cupric sulfate solution, dried (magnesium sulfate), filtered, and concentrated in vacuo. The residue was chromatographed (silica gel, methylene chloride to 20% ethyl acetate/80% methylene chloride) to give 400 mg (95%) of the the title compound as a solid.

Workup

  1. washwashed with saturated aqueous cupric sulfate solution
  2. dry with materialdried (magnesium sulfate)
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customThe residue was chromatographed (silica gel, methylene chloride to 20% ethyl acetate/80% methylene chloride)

Sources & evidence

ORD record
ord-384ac40e3e5c40b68956e66c5735ea43
Source dataset
uspto-grants-2001_11
Patent number
US06313122B1

Linked notes

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