Methanesulfonyl chloride → 2-Morpholinoethyl methanesulfonate

HRID 415083Notes

Reaction equation

HRID 415083 reaction equation
[O:1]1[CH2:6][CH2:5][N:4]([CH2:7][CH2:8][OH:9])[CH2:3][CH2:2]1.CCN(C(C)C)C(C)C.[S:19](Cl)([CH3:22])(=[O:21])=[O:20]>ClCCl>[CH3:22][S:19]([O:9][CH2:8][CH2:7][N:4]1[CH2:5][CH2:6][O:1][CH2:2][CH2:3]1)(=[O:21])=[O:20]

Participants

5

Reactant 3

HCID 31297Methanesulfonyl chlorideHCID 611632-MorpholinoethanolHCID 81531Diisopropylethylamine

Product 1

HCID 593495932-Morpholinoethyl methanesulfonate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A flask was charged with 2-morpholinoethanol (1.0 g, 7.1 mmol), DIEA (2.4 mL, 14 mmol) and dichloromethane (100 mL). Mesylchloride (0.64 mL, 8.3 mmol) was added in a dropwise fashion to the dichloromethane mixture and the reaction mixture was stirred at room temperature for 15 hours. Concentration of the reaction mixture gave rise to a quantitative yield of 2-morpholinoethyl methanesulfonate, which was used in the next step without any without further purification. EI (MS); 210 (MH+).

Sources & evidence

ORD record
ord-5ecb0ee9bb444946a2913d864021b5e2
Source dataset
uspto-grants-2012_01
Patent number
US08088767B2

Reaction notes

Loading…