Triethylamine → N-(2-(4-bromo-3,5-dimethylphenoxy)ethyl)methanesulfonamide

HRID 237544Notes

Reaction equation

[Br:1][C:2]1[C:11]([CH3:12])=[CH:10][C:5]([O:6][CH2:7][CH2:8][NH2:9])=[CH:4][C:3]=1[CH3:13].C(N(CC)CC)C.[CH3:21][S:22](Cl)(=[O:24])=[O:23]>ClCCl>[Br:1][C:2]1[C:11]([CH3:12])=[CH:10][C:5]([O:6][CH2:7][CH2:8][NH:9][S:22]([CH3:21])(=[O:24])=[O:23])=[CH:4][C:3]=1[CH3:13]

Participants

Conditions

Temperature: 0 °C

Procedure

To a cooled (0° C.) solution of 2-(4-bromo-3,5-dimethylphenoxy)ethanamine (100 mg) and triethylamine (63 μL) in dichloromethane (2 mL) is added methanesulfonyl chloride (32 μL). The mixture is stirred for 2 hours at 0° C. Then the mixture is partitioned between dichloromethane and water. The organic phase is separated, washed with brine and dried (MgSO4). The solvent is evaporated and the residue is purified by HPLC on reversed phase to give the title compound. Yield: 90 mg; LC (method 7): tR=1.01 min; Mass spectrum (ESI+): m/z=322 [M+H]+.

Workup

customThen the mixture is partitioned between dichloromethane and water
customThe organic phase is separated
washwashed with brine
dry with materialdried (MgSO4)
customThe solvent is evaporated
customthe residue is purified by HPLC on reversed phase

Sources & evidence

ORD record: ord-5bdcf8c67df74aa5851c07702d842fbb
Source dataset: uspto-grants-2014_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08642585B2

Reaction notes

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