Diisopropylethylamine → HCID 178518106, compound

HRID 1620614Notes

Reaction equation

HRID 1620614 reaction equation
S=[C:2]1[CH2:6][S:5][C:4](=[O:7])[NH:3]1.Cl.[O:9]1[CH:13]=[CH:12][C:11]([CH2:14][NH2:15])=[N:10]1.C(N(C(C)C)C(C)C)C>C(O)C>[O:9]1[CH:13]=[CH:12][C:11]([CH2:14][NH:15][C:2]2[CH2:6][S:5][C:4](=[O:7])[N:3]=2)=[N:10]1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 15395954-Sulfanylidene-1,3-thiazolidin-2-oneHCID 446076513-Isoxazolemethanamine, hydrochloride (1:1)

Product 1

HCID 178518106HCID 178518106, compoundYield 49.5%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 4-thioxo-1,3-thiazolidin-2-one (700 mg) in ethanol (20 mL) were added (isoxazol-3-ylmethyl)amine hydrochloride (707 mg) and N-ethyl-N-(1-methylethyl)propan-2-amine (1.42 mL), and the mixture was heated under reflux overnight. The reaction mixture was concentrated, the residue was purified by silica gel column chromatography (methanol/ethyl acetate), and the obtained powder was washed with ethyl acetate to give the title compound (513 mg).

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux overnight
  3. concentrationThe reaction mixture was concentrated
  4. customthe residue was purified by silica gel column chromatography (methanol/ethyl acetate)
  5. washthe obtained powder was washed with ethyl acetate

Sources & evidence

ORD record
ord-a455bbc4d12040d89621d8c75b7e3ae2
Source dataset
uspto-grants-2014_07
Patent number
US08772277B2

Reaction notes

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