Acetone → HCID 58957422, compound

HRID 2075297Notes

Reaction equation

HRID 2075297 reaction equation
[CH3:1][C:2]([CH3:4])=O.[CH2:5]([N:8]1[C:12](=[O:13])[CH2:11][NH:10][C:9]1=[S:14])[CH:6]=[CH2:7].N1CCOCC1>C(OCC)(=O)C>[CH2:5]([N:8]1[C:12](=[O:13])[C:11](=[C:2]([CH3:4])[CH3:1])[NH:10][C:9]1=[S:14])[CH:6]=[CH2:7]

Participants

5

Reactant 3

HCID 180AcetoneHCID 8083MorpholineHCID 3032418Hydantoin, 3-allyl-2-thioxo-

Product 1

HCID 58957422HCID 58957422, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

A flask equipped with a reflux condenser and nitrogen atmosphere was charged with acetone (20 mL), 3-allylthiohydantoin (2.0 g, 0.013 mol), and morpholine (1.1 g, 0.013 mol). The mixture was heated at reflux for 80 min and, after cooling, was diluted with 40 mL of ethyl acetate. The resulting solution was washed with 2×20 mL 1.2 M HCl, 20 mL of water, and 20 mL of saturated aqueous NaCl. The solution was then filtered through 1 PS paper and concentrated to dryness at aspirator pressure and then high vacuum. The off-white crystalline residue weighed 2.3 g (92%). No other components were detectable by HPLC at 215 nm. NMR (CDCl3) δ 9.9 (bs, 1H), 5.1-6.1 (m, 3H), 4.6 (d, 2H), 2.3 (s, 3H), 2.0 (s, 3H).

Workup

  1. customA flask equipped with a reflux condenser
  2. temperatureThe mixture was heated
  3. temperatureat reflux for 80 min
  4. temperatureafter cooling
  5. washThe resulting solution was washed with 2×20 mL 1.2 M HCl, 20 mL of water, and 20 mL of saturated aqueous NaCl
  6. filtrationThe solution was then filtered through 1 PS paper
  7. concentrationconcentrated to dryness at aspirator pressure

Sources & evidence

ORD record
ord-9b2fa6d0c8084e05acf8e68658048d59
Source dataset
uspto-grants-2011_04
Patent number
US07919630B2

Reaction notes

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