Methyl iodide → N-[2-(3-amidinophenoxy)ethyl]-4-(3,4-dimethoxybenzoyl)benzamide

HRID 2414438노트

반응식

HRID 2414438 반응식
[C:1]([C:3]1[CH:4]=[C:5]([CH:30]=[CH:31][CH:32]=1)[O:6][CH2:7][CH2:8][NH:9][C:10](=[O:29])[C:11]1[CH:16]=[CH:15][C:14]([C:17](=[O:28])[C:18]2[CH:23]=[CH:22][C:21]([O:24][CH3:25])=[C:20]([O:26][CH3:27])[CH:19]=2)=[CH:13][CH:12]=1)#[N:2].O.O.S.[Na].O.O.O.O.O.O.[Cl-].[Mg+2].[Cl-].CI.C([O-])(=O)C.[NH4+:52]>CN(C)C=O.CC(C)=O>[C:1]([C:3]1[CH:4]=[C:5]([CH:30]=[CH:31][CH:32]=1)[O:6][CH2:7][CH2:8][NH:9][C:10](=[O:29])[C:11]1[CH:12]=[CH:13][C:14]([C:17](=[O:28])[C:18]2[CH:23]=[CH:22][C:21]([O:24][CH3:25])=[C:20]([O:26][CH3:27])[CH:19]=2)=[CH:15][CH:16]=1)(=[NH:52])[NH2:2]

참가 물질

8

반응물 5

HCID 6328Methyl iodideHCID 24644Magnesium chloride hexahydrateHCID 517165Ammonium AcetateHCID 22645151N-[2-(3-cyanophenoxy)ethyl]-4-(3,4-dimethoxybenzoyl)benzamideHCID 86584117Sodium hydrogen sulfide dihydrate

생성물 1

HCID 9872556N-[2-(3-amidinophenoxy)ethyl]-4-(3,4-dimethoxybenzoyl)benzamide

시약·촉매·용매 2

HCID 180Acetone용매HCID 6228Dimethylformamide용매

실험 절차

0.5 g (1.16 mmol) of N-[2-(3-cyanophenoxy)ethyl]-4-(3,4-dimethoxybenzoyl)benzamide was dissolved in 10 ml of N,N-dimethylformamide (dehydrated). 0.21 g (2.32 mmol) of sodium hydrogensulfide dihydrate and 0.24 g (1.16 mmol) of magnesium chloride hexahydrate were added to the obtained solution under cooling with ice, and they were stirred at room temperature for 2.5 hours. After the treatment with ethyl acetate as the extraction solvent in an ordinary manner, the solvent was evaporated, and the obtained crude product was dissolved in 20 ml of acetone. 0.56 ml (9.0 mmol) of methyl iodide was added to the solution, and they were refluxed for 3 hours. The solvent was evaporated, and the obtained crude product was washed with ethyl acetate. After the filtration, the obtained crystals were dissolved in 10 ml of methanol. 155 mg (2.0 mmol) of ammonium acetate was added to the obtained solution, and they were stirred for 3 hours. The solvent was evaporated, and the residue was treated in the same manner as that in step 7 in Example 51 to obtain the title compound.

후처리

  1. temperatureunder cooling with ice, and they
  2. customAfter the treatment with ethyl acetate as the extraction solvent in an ordinary manner, the solvent was evaporated
  3. customthe obtained crude product
  4. temperaturewere refluxed for 3 hours
  5. customThe solvent was evaporated
  6. customthe obtained crude product
  7. washwas washed with ethyl acetate
  8. filtrationAfter the filtration
  9. dissolutionthe obtained crystals were dissolved in 10 ml of methanol
  10. stirringwere stirred for 3 hours
  11. customThe solvent was evaporated
  12. additionthe residue was treated in the same manner as that in step 7 in Example 51

출처 및 근거

ORD 기록
ord-2fc9bcdb5a284233b9c94c4376d922c9
출처 데이터셋
uspto-grants-2004_11
특허 번호
US06812231B2

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