Methanesulfonyl chloride → 4-(Methanesulfonylamino)benzenebutanol methanesulfonate
Reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][CH2:10][CH2:11][OH:12])=[CH:4][CH:3]=1.[CH3:13][S:14](Cl)(=[O:16])=[O:15]>N1C=CC=CC=1>[CH3:13][S:14]([O:12][CH2:11][CH2:10][CH2:9][CH2:8][C:5]1[CH:4]=[CH:3][C:2]([NH:1][S:14]([CH3:13])(=[O:16])=[O:15])=[CH:7][CH:6]=1)(=[O:16])=[O:15]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- -10 °C
Procedure
9.25 g (0.056 mole) 4-aminobenzenebutanol is dissolved in 100 ml pyridine and the solution is cooled to ca. -10° C. 17.33 ml (25.65 g) (0.244 mole) methanesulfonyl chloride is added dropwise with vigorous stirring at a rate such that the reaction temperature does not rise beyond -5° C. After all methanesulfonyl chloride is added, the reaction mixture is left in the freezer for two days. The reaction mixture is poured onto 300 ml ice water and extracted with 3×200 ml methylene chloride. The combined organic layers are washed with 1 liter cold 5% HCl in 3 portions. The organic layer is dried over sodium sulfate, filtered, and stripped. The residue is crystallized from ethyl acetate/ether to obtain the title compound.
Workup
- customdoes not rise beyond -5° C
- extractionextracted with 3×200 ml methylene chloride
- washThe combined organic layers are washed with 1 liter cold 5% HCl in 3 portions
- dry with materialThe organic layer is dried over sodium sulfate
- filtrationfiltered
- customThe residue is crystallized from ethyl acetate/ether
Sources & evidence
- ORD record
- ord-d0df65651268455d9a7aa0f9b89b5d07
- Source dataset
- uspto-grants-1986_04
- Patent number
- US04581370
Reaction notes
Loading…