2-Furanmethanethiol → N-furfurylthioethylpropionamide
Reaction equation
[CH2:1]([SH:7])[C:2]1[O:6][CH:5]=[CH:4][CH:3]=1.[CH2:8]([C:10]1[O:11][CH2:12][CH2:13][N:14]=1)[CH3:9]>>[CH2:1]([S:7][CH2:12][CH2:13][NH:14][C:10](=[O:11])[CH2:8][CH3:9])[C:2]1[O:6][CH:5]=[CH:4][CH:3]=1Participants
Procedure
In this example furfurylmercaptan and 2-ethyl-2-oxazoline are reacted to form N-furfurylthioethylpropionamide. Furfurylmercaptan (13.04 grams, 0.11 mols) is heated under nitrogen to 155° C. in a flask. 2-Ethyl-2-oxazoline (11.4 grams, 0.115 mols) is slowly added from a dropping funnel over a period of two hours. The mixture is post-reacted at 155° C. for an additional 11/2 hours. The product is isolated by distillation at reduced pressure: BP 136°-137° C. at 0.2 millimeters Hg. The spectral and elemental analyses correspond to those of the N-furfurylthioethylpropionamide mentioned above. Analysis for the crude reaction mixture by internal standard gas/liquid chromatography shows 1.7 weight percent 2-ethyl-2-oxazoline, 0.8 weight percent furfurylmercaptan and 95.8 weight percent N-(2-furfurylthioethyl)propionamide. This is a reaction yield based on starting materials of 96 percent.
Sources & evidence
- ORD record
- ord-0fca1314b67949dab1d2b89aaaf31958
- Source dataset
- uspto-grants-1985_09
- Patent number
- US04539416
Reaction notes
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