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

HRID 397539

Reaction equation

HRID 397539 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-8e63c8578ab04ca1b7d062c795c3e082
Source dataset
uspto-grants-2003_08
Patent number
US06610704B1

Linked notes

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