Homoveratrylamine → HCID 59351455, compound

HRID 1889302Notes

Reaction equation

HRID 1889302 reaction equation
[NH2:1][C:2]1[S:3][C:4]([CH2:11][CH3:12])=[CH:5][C:6]=1[C:7]([O:9]C)=O.Cl[C:14](Cl)([O:16]C(=O)OC(Cl)(Cl)Cl)Cl.C(N(CC)CC)C.[CH3:32][O:33][C:34]1[CH:35]=[C:36]([CH2:42][CH2:43][NH2:44])[CH:37]=[CH:38][C:39]=1[O:40][CH3:41]>C(Cl)Cl>[CH3:32][O:33][C:34]1[CH:35]=[C:36]([CH2:42][CH2:43][N:44]2[C:7](=[O:9])[C:6]3[CH:5]=[C:4]([CH2:11][CH3:12])[S:3][C:2]=3[NH:1][C:14]2=[O:16])[CH:37]=[CH:38][C:39]=1[O:40][CH3:41]

Participants

6

Reactant 4

HCID 8421HomoveratrylamineHCID 8471TriethylamineHCID 94429TriphosgeneHCID 7370942-Amino-5-ethyl-3-thiophenecarboxylic acid methyl ester

Product 1

HCID 59351455HCID 59351455, compoundYield 95%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution (40 mL) of methyl 2-amino-5-ethylthiophene-3-carboxylate (0.5 g) in methylene chloride were added triphosgene (0.32 g) and triethylamine (0.59 mL), and the mixture was stirred at room temperature for 2 hr. To the reaction mixture was added 2-(3,4-dimethoxyphenyl)ethanamine (1.36 mL), and the mixture was further stirred at room temperature for 1 hr. The reaction mixture was washed with water and saturated brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure. The obtained residue was dissolved in methanol (20 mL), sodium methoxide (28% methanol solution, 1.3 g) was added, and the mixture was stirred at 60° C. for 2 hr. The reaction mixture was neutralized with hydrochloric acid (10% methanol solution), insoluble material was filtered off, and the solvent was evaporated under reduced pressure. The precipitated solid was collected by filtration to give the title compound as a colorless solid (0.92 g, 95%).

Workup

  1. stirringthe mixture was further stirred at room temperature for 1 hr
  2. washThe reaction mixture was washed with water and saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customThe solvent was evaporated under reduced pressure
  5. dissolutionThe obtained residue was dissolved in methanol (20 mL)
  6. additionsodium methoxide (28% methanol solution, 1.3 g) was added
  7. stirringthe mixture was stirred at 60° C. for 2 hr
  8. filtrationwas filtered off
  9. customthe solvent was evaporated under reduced pressure
  10. filtrationThe precipitated solid was collected by filtration

Sources & evidence

ORD record
ord-eb75c37d45944b26af18007b11313e77
Source dataset
uspto-grants-2013_08
Patent number
US08501750B2

Reaction notes

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