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

HRID 397539

반응식

HRID 397539 반응식
[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

참가 물질

7

반응물 4

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

생성물 1

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

시약·촉매·용매 2

HCID 1140Toluene용매HCID 6344Dichloromethane용매

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-8e63c8578ab04ca1b7d062c795c3e082
출처 데이터셋
uspto-grants-2003_08
특허 번호
US06610704B1

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