HCID 20512987, compound → HCID 13092376, compound

HRID 1164260Notes

Reaction equation

HRID 1164260 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([CH2:8][CH3:9])[C:3]=1[NH:10][CH:11]1[CH2:15][CH2:14][O:13][C:12]1=O.C([O-])(=[S:19])C.[K+]>COCCOCCOC>[CH3:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([CH2:8][CH3:9])[C:3]=1[NH:10][CH:11]1[CH2:15][CH2:14][S:19][C:12]1=[O:13]

Participants

4

Reactant 2

HCID 20512987HCID 20512987, compoundHCID 23670855Potassium ethanethioate

Product 1

HCID 13092376HCID 13092376, compoundYield 44.2%

Reagents, catalysts & solvents 1

HCID 8150DiglymeSolvent

Conditions

Temperature
150 °C

Procedure

11 g (0.05 mol) of N-(2-methyl-6-ethylphenyl)amino-tetrahydrofuran-2-one and 6.6 g (0.05 mol) of potassium thioacetate are dissolved in 200 ml of diethylene glycol dimethyl ether and the solution is stirred for 20 hours at 150° C. After cooling, the mixture is poured into ice-water and extracted with methylene chloride. The combined extracts are washed repeatedly with water, dried over sodium sulfate and filtered and the filtrate is concentrated. After distillation under a high vacuum, the residue yields 5.2 g (44.2% of theory) of N-(2-methyl-6-ethylphenyl)-amino-tetrahydrothiophen-2-one. Boiling point 160°-165° C. under 0.45 mm Hg.

Workup

  1. temperatureAfter cooling
  2. extractionextracted with methylene chloride
  3. washThe combined extracts are washed repeatedly with water
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. concentrationthe filtrate is concentrated
  7. distillationAfter distillation under a high vacuum

Sources & evidence

ORD record
ord-a78838b66e9d43c28d19dbd0a4620b0e
Source dataset
uspto-grants-1983_01
Patent number
US04368327

Reaction notes

Loading…