Triethylamine → HCID 59351787, compound

HRID 1889305Notes

Reaction equation

HRID 1889305 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.ClC(Cl)(O[C:17](=[O:23])OC(Cl)(Cl)Cl)Cl.C(N(CC)CC)C.[C:32]1([NH:38][CH2:39][CH2:40][NH2:41])[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1>C(Cl)Cl>[NH:38]([CH2:39][CH2:40][N:41]1[C:7](=[O:9])[C:6]2[CH:5]=[C:4]([CH2:11][CH3:12])[S:3][C:2]=2[NH:1][C:17]1=[O:23])[C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 742701,2-Ethanediamine, N1-phenyl-HCID 94429TriphosgeneHCID 7370942-Amino-5-ethyl-3-thiophenecarboxylic acid methyl ester

Product 1

HCID 59351787HCID 59351787, compoundYield 64.7%

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 N-phenylethane-1,2-diamine (1 g), 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 concentrated under reduced pressure, and the obtained residue was extracted with 1N hydrochloric acid and ethyl acetate. The ethyl acetate layer was washed with saturated brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure. The obtained solid was recrystallized from tetrahydrofuran-hexane to give the title compound as colorless crystals (0.22 g, 25%).

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. concentrationThe reaction mixture was concentrated under reduced pressure
  9. extractionthe obtained residue was extracted with 1N hydrochloric acid and ethyl acetate
  10. washThe ethyl acetate layer was washed with saturated brine
  11. dry with materialdried over anhydrous magnesium sulfate
  12. customThe solvent was evaporated under reduced pressure
  13. customThe obtained solid was recrystallized from tetrahydrofuran-hexane

Sources & evidence

ORD record
ord-f10020724b024e65bb1f5d21c38e5b9c
Source dataset
uspto-grants-2013_08
Patent number
US08501750B2

Reaction notes

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