Phenethylamine → HCID 59351801, compound

HRID 1889401Notes

Reaction equation

HRID 1889401 reaction equation
[NH2:1][C:2]1[S:6][C:5]([CH2:7][CH3:8])=[N:4][C:3]=1[C:9]([O:11]CC)=O.ClC(Cl)(O[C:18](=[O:24])OC(Cl)(Cl)Cl)Cl.C(N(CC)CC)C.[C:33]1([CH2:39][CH2:40][NH2:41])[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1>C(Cl)Cl>[CH2:7]([C:5]1[S:6][C:2]2[NH:1][C:18](=[O:24])[N:41]([CH2:40][CH2:39][C:33]3[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=3)[C:9](=[O:11])[C:3]=2[N:4]=1)[CH3:8]

Participants

6

Reactant 4

HCID 1001PhenethylamineHCID 8471TriethylamineHCID 94429TriphosgeneHCID 23627814HCID 23627814, compound

Product 1

HCID 59351801HCID 59351801, compoundYield 64%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution (30 mL) of ethyl 5-amino-2-ethyl-1,3-thiazole-4-carboxylate (0.5 g) in methylene chloride were added triphosgene (0.32 g) and triethylamine (0.23 mL), and the mixture was stirred at room temperature for 2 hr. To the reaction mixture was added 2-phenylethanamine (0.95 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 ethanol (40 mL), sodium ethoxide (20% ethanol solution, 2.2 g) was added, and the mixture was stirred at 80° 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 precipitated solid was collected by filtration to give the title compound as a colorless solid (0.48 g, 64%).

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 ethanol (40 mL)
  6. additionsodium ethoxide (20% ethanol solution, 2.2 g) was added
  7. stirringthe mixture was stirred at 80° 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. filtrationThe precipitated solid was collected by filtration

Sources & evidence

ORD record
ord-7b1007e3754d4d02859a39305571cf39
Source dataset
uspto-grants-2013_08
Patent number
US08501750B2

Reaction notes

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