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

HRID 2187961Notes

Reaction equation

HRID 2187961 reaction equation
[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]

Participants

8

Reactant 5

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

Product 1

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

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 6228DimethylformamideSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-a3719ea7597c4f5cbe1a9c33c5f94f6b
Source dataset
uspto-grants-2002_06
Patent number
US06410538B2

Reaction notes

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