Pyridine → N1-(4-Methoxybenzoyl)-N2-[4-(4-morpholinyl)benzyl]-1,2-benzenediamine

HRID 49833

Reaction equation

HRID 49833 reaction equation
[N:1]1([C:7]2[CH:14]=[CH:13][C:10]([CH2:11]O)=[CH:9][CH:8]=2)[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1.C(Cl)(Cl)=O.[CH3:19][O:20][C:21]1[CH:36]=[CH:35][C:24]([C:25]([NH:27][C:28]2[C:29]([NH2:34])=[CH:30][CH:31]=[CH:32][CH:33]=2)=[O:26])=[CH:23][CH:22]=1.N1C=CC=CC=1>C1(C)C=CC=CC=1.C(Cl)Cl>[CH3:19][O:20][C:21]1[CH:22]=[CH:23][C:24]([C:25]([NH:27][C:28]2[C:29]([NH:34][CH2:11][C:10]3[CH:13]=[CH:14][C:7]([N:1]4[CH2:6][CH2:5][O:4][CH2:3][CH2:2]4)=[CH:8][CH:9]=3)=[CH:30][CH:31]=[CH:32][CH:33]=2)=[O:26])=[CH:35][CH:36]=1

Participants

7

Reactant 4

HCID 1049PyridineHCID 6371PhosgeneHCID 785232N-(2-Aminophenyl)-4-methoxybenzamideHCID 2776456[4-(Morpholin-4-yl)phenyl]methanol

Product 1

HCID 9844868N1-(4-Methoxybenzoyl)-N2-[4-(4-morpholinyl)benzyl]-1,2-benzenediamineYield 14%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 6344DichloromethaneSolvent

Procedure

4-(4-Morpholinyl)benzyl alcohol (150 mg, 0.78 mmol) was added to a solution of phosgene in toluene (1.93 M, 1.2 mL). After 4 h, the mixture was treated with a solution of N1-(4-methoxybenzoyl)-1,2-benzenediamine (188 mg, 0.78 mmol) and pyridine (2 mL) in methylene chloride (3 mL). After 16 h, the mixture was concentrated and the residue was dissolved in EtOAc. The organic layer was washed with water (4×), brine (1×), dried with potassium carbonate, and concentrated. The residue was purified by chromatography (SiO2, 5 to 15% EtOAc in CH2Cl2), yielding 45 mg (14%) of the title compound.

Workup

  1. waitAfter 16 h
  2. concentrationthe mixture was concentrated
  3. dissolutionthe residue was dissolved in EtOAc
  4. washThe organic layer was washed with water (4×), brine (1×)
  5. dry with materialdried with potassium carbonate
  6. concentrationconcentrated
  7. customThe residue was purified by chromatography (SiO2, 5 to 15% EtOAc in CH2Cl2)

Sources & evidence

ORD record
ord-3cb00663c5514b80ae1b7ade829f69c8
Source dataset
uspto-grants-2004_03
Patent number
US06710057B2

Linked notes

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