Tetrahydrofuran → 5-Cyanomethyl-4-methyl-3-oxothiomorpholine
Reaction equation
C([N:3](CC)CC)C.[CH3:8][NH:9][C:10](=[O:13])[CH2:11][SH:12].O1[CH2:18][CH2:17][CH2:16][CH2:15]1>O>[C:18]([CH2:17][CH:16]1[N:9]([CH3:8])[C:10](=[O:13])[CH2:11][S:12][CH2:15]1)#[N:3]Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 0 °C
Procedure
To a solution of omega-cyano-allyl bromide (9.07 g) in tetrahydrofurane (60 ml) cooled at -65° C. is added a mixture of triethylamine (9.5 ml) and thioglycolic methylamide (6.13 ml). After 15 minutes, cooling is stopped and the mixture is warmed to 0° C. The mixture is diluted with water and extracted with ethyl acetate. The extract is washed with water, dried, and concentrated to give 5-cyanomethyl-4-methyl-3-oxothiomorpholine (6.86 g).
Workup
- additionis added
- temperaturecooling
- extractionextracted with ethyl acetate
- washThe extract is washed with water
- customdried
- concentrationconcentrated
Sources & evidence
- ORD record
- ord-f2f875b9e1b44ee1bf768e8bf112f391
- Source dataset
- uspto-grants-1986_03
- Patent number
- US04578378
Reaction notes
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