Methanesulfonyl chloride → HCID 53967418, compound
Reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([C:7]([CH2:9][CH2:10][CH2:11][CH2:12]O)=[O:8])[CH:2]=1.C(N(CC)C(C)C)(C)C.CS(Cl)(=O)=O.[C:28]([OH:31])(=[S:30])[CH3:29]>O1CCCC1.O>[C:28]([S:30][CH2:12][CH2:11][CH2:10][CH2:9][C:7](=[O:8])[C:3]1[CH:4]=[CH:5][CH:6]=[N:1][CH:2]=1)(=[O:31])[CH3:29]Participants
Conditions
- Temperature
- 0 °C
Procedure
A solution of 4-hydroxybutyl 3-pyridyl ketone (89.6 g) in tetrahydrofuran (750 ml) under nitrogen at room temperature is treated with N,N-diisopropylethylamine (155.1 g). The mixture is then cooled to 0° C. and treated with methanesulphonyl chloride (63.0 g) continually during 10 minutes, maintaining the temperature at between 5° C. and 10° C., and then the mixture is stirred for 10 minutes. It is then treated with thioacetic acid (45.7 g) during 10 minutes and allowed to warm to 35° C. It is stirred for 1 hour at 35° C. and then cooled to 20° C. It is then treated with water (750 ml) during 5 minutes and the mixture is extracted twice with toluene (750 ml and 350 ml). The combined extracts are washed with water and evaporated, to give S-(4-nicotinoylbutyl) thioacetate (113.4 g), in the form of an oil.
Workup
- temperaturemaintaining the temperature at between 5° C. and 10° C.
- temperatureto warm to 35° C
- stirringIt is stirred for 1 hour at 35° C.
- temperaturecooled to 20° C
- extractionthe mixture is extracted twice with toluene (750 ml and 350 ml)
- washThe combined extracts are washed with water
- customevaporated
Sources & evidence
- ORD record
- ord-c2ca06d20dca466bb873b2948fcb2868
- Source dataset
- uspto-grants-1997_11
- Patent number
- US05688954
Reaction notes
Loading…