Triethylamine → HCID 79006302, compound

HRID 78502Notes

Reaction equation

HRID 78502 reaction equation
Br[CH:2]1[C:6]([CH3:8])([CH3:7])[O:5][C:4]([CH3:10])([CH3:9])[C:3]1=O.[NH2:12][C:13]([NH2:15])=[S:14].C(N(CC)CC)C>C(O)C>[CH3:7][C:6]1([CH3:8])[C:2]2[N:12]=[C:13]([NH2:15])[S:14][C:3]=2[C:4]([CH3:10])([CH3:9])[O:5]1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 2723790ThioureaHCID 122017454-Bromo-2,2,5,5-tetramethyldihydrofuran-3(2h)-one

Product 1

HCID 79006302HCID 79006302, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of Example 248A (10.0 g, 0.045 mol) in ethanol (100 mL) were added thiourea (3.8 g, 0.05 mol) and triethylamine (6.3 mL, 0.045 mol). The reaction mixture was heated at reflux overnight, then cooled, and concentrated under reduced pressure. The residue was diluted with water (25 mL) and extracted with ethyl acetate (3×50 mL). The combined organic extracts were dried (Na2SO4), filtered and concentrated. The residue was purified by column chromatography (SiO2, 0-5% methanol in CH2Cl2) to afford the title compound. MS (ESI+) m/z 199 (M+H)+.

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureat reflux overnight
  3. temperaturecooled
  4. concentrationconcentrated under reduced pressure
  5. additionThe residue was diluted with water (25 mL)
  6. extractionextracted with ethyl acetate (3×50 mL)
  7. dry with materialThe combined organic extracts were dried (Na2SO4)
  8. filtrationfiltered
  9. concentrationconcentrated
  10. customThe residue was purified by column chromatography (SiO2, 0-5% methanol in CH2Cl2)

Sources & evidence

ORD record
ord-8fcb8b0e9d8d40428d516bffd4312d71
Source dataset
uspto-grants-2014_09
Patent number
US08841334B2

Reaction notes

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