Triethylamine → HCID 178448893, compound

HRID 1620731Notes

Reaction equation

HRID 1620731 reaction equation
S=[C:2]1[CH2:6][S:5][C:4](=[O:7])[NH:3]1.Cl.[CH3:9][CH:10]([NH2:13])[C:11]#[CH:12].C(N(CC)CC)C>C(O)C>[CH3:9][CH:10]([NH:13][C:2]1[CH2:6][S:5][C:4](=[O:7])[N:3]=1)[C:11]#[CH:12]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 15395954-Sulfanylidene-1,3-thiazolidin-2-oneHCID 12632905But-3-yn-2-amine--hydrogen chloride (1/1)

Product 1

HCID 178448893HCID 178448893, compoundYield 56.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 4-thioxo-1,3-thiazolidin-2-one (2 g) in ethanol (35 mL) were added but-3-yn-2-amine hydrochloride (2.38 g) and triethylamine (3.14 mL), and the mixture was stirred at room temperature for 4 hr. The reaction mixture was concentrated, water was added to the residue, and the mixture was extracted with ethyl acetate. The extract was washed with water and saturated brine, and dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. The residue was washed with ethyl acetate to give the title compound (1.42 g).

Workup

  1. concentrationThe reaction mixture was concentrated
  2. additionwater was added to the residue
  3. extractionthe mixture was extracted with ethyl acetate
  4. washThe extract was washed with water and saturated brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customthe solvent was evaporated under reduced pressure
  7. washThe residue was washed with ethyl acetate

Sources & evidence

ORD record
ord-ee0d0aeb43a645628469e855af5e7439
Source dataset
uspto-grants-2014_07
Patent number
US08772277B2

Reaction notes

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