HCID 20512987, compound → HCID 13092376, compound

HRID 1164259Notes

Reaction equation

HRID 1164259 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.[NH4+]>CS(C)=O>[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 178477230HCID 178477230, compound

Product 1

HCID 13092376HCID 13092376, compoundYield 48.5%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

11 g (0.05 mol) of N-(2-methyl-6-ethylphenyl)amino-tetrahydrofuran-2-one and 4.7 g (0.05 mol) of ammonium thioacetate are stirred in 80 ml of dimethylsulfoxide at 90° to 100° C. After cooling, the solution is poured into ice-water and extracted with methylene chloride. The combined extracts are repeatedly washed with water, dried over sodium sulfate and filtered and the filtrate is concentrated. Distillation of the residue under a high vacuum yields 5.7 g (48.5% of theory) of colourless N-(2-methyl-6-ethylphenyl)-amino-tetrahydrothiophen-2-one. Boiling point 167°-173° C. under 0.5 mm Hg.

Workup

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

Sources & evidence

ORD record
ord-a0336c1f486c45e5aeef96d1fdab0ce7
Source dataset
uspto-grants-1983_01
Patent number
US04368327

Reaction notes

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