Methanesulfonyl chloride → 2-(2,3-Dihydro-1,4-benzoxazin-4-yl)ethyl methanesulfonate
Reaction equation
[O:1]1[C:6]2[CH:7]=[CH:8][CH:9]=[CH:10][C:5]=2[N:4]([CH2:11][CH2:12][OH:13])[CH2:3][CH2:2]1.[CH3:14][S:15](Cl)(=[O:17])=[O:16]>N1C=CC=CC=1>[CH3:14][S:15]([O:13][CH2:12][CH2:11][N:4]1[C:5]2[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=2[O:1][CH2:2][CH2:3]1)(=[O:17])=[O:16]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 25 °C
Procedure
To a solution of 2-(2,3-dihydro-1,4-benzoxazin-4-yl)ethanol (17.0 g, 94.9 mmol) in pyridine (200 ml) was added methanesulfonyl chloride (16.31 g, 142.0 mmol) dropwise at 0° C. The reaction mixture was stirred for 10 h at 25° C. Ice water (200 ml) was added and the mixture was extracted with ethyl acetate (2×100 ml). The combined organic extracts were washed with 2N HCl (3×75 ml), water (75 ml), brine (50 ml) and dried (Na2SO4). The solvent was evaporated under reduced pressure. The residue was triturated with 5% ethyl acetate in pet. ether to afford the title compound (15.0 g, 61%) as brown solid. mp. 92-95° C.
Workup
- extractionthe mixture was extracted with ethyl acetate (2×100 ml)
- washThe combined organic extracts were washed with 2N HCl (3×75 ml), water (75 ml), brine (50 ml)
- dry with materialdried (Na2SO4)
- customThe solvent was evaporated under reduced pressure
- customThe residue was triturated with 5% ethyl acetate in pet. ether
Sources & evidence
- ORD record
- ord-9244b5e0d6cf4188a20890cf0cb75f59
- Source dataset
- uspto-grants-2000_12
- Patent number
- US06159966
Reaction notes
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