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

HRID 49833

反応式

HRID 49833 の反応式
[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

参加物

7

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 1140Toluene溶媒HCID 6344Dichloromethane溶媒

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-3cb00663c5514b80ae1b7ade829f69c8
出典データセット
uspto-grants-2004_03
特許番号
US06710057B2

関連ノート

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