Hexachloroethane → 2-Chloro-N-(5-chloro-3-methoxy-2-pyrazinyl)-3-fluorobenzenesulphonamide

HRID 1444033Notes

Reaction equation

[Cl:1][C:2]1[N:3]=[C:4]([O:19][CH3:20])[C:5]([NH:8][S:9]([C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([F:18])[CH:13]=2)(=[O:11])=[O:10])=[N:6][CH:7]=1.C([N-]C(C)C)(C)C.[Li+].[Cl:29]C(Cl)(Cl)C(Cl)(Cl)Cl>O1CCCC1>[Cl:29][C:13]1[C:14]([F:18])=[CH:15][CH:16]=[CH:17][C:12]=1[S:9]([NH:8][C:5]1[C:4]([O:19][CH3:20])=[N:3][C:2]([Cl:1])=[CH:7][N:6]=1)(=[O:11])=[O:10]

Participants

Conditions

Temperature: -78 °C

Procedure

A solution of N-(5-chloro-3-methoxy-2-pyrazinyl)-3-fluorobenzenesulphonamide (Example 130a) (0.159 g) in dry tetrahydrofuran (3 mL) was added to a stirred solution of lithium di-iso-propylamide (prepared from di-iso-propylamine (0.151 g) and n-butyl lithium (2.5M in hexanes)) in tetrahydrofuran (7.0 mL) at −78° C. The resulting solution was stirred at −78° C. for 15 minutes and then hexachloroethane (0.472 g) in tetrahydrofuran (2 mL) was added and the mixture allowed to attain room temperature over a 5 hour period. The reaction was quenched by the addition of 1N hydrochloric acid (10 mL) and extracted into ethyl acetate (2×20 mL). The combined extracts were dried (MgSO4), filtered and concentrated to afford an oil that was purified by chromatography on silica gel eluting with ethyl acetate/iso-hexane mixtures gave the titled compound (0.086 g) as a white solid.

Workup

waitto attain room temperature over a 5 hour period
customThe reaction was quenched by the addition of 1N hydrochloric acid (10 mL)
extractionextracted into ethyl acetate (2×20 mL)
dry with materialThe combined extracts were dried (MgSO4)
filtrationfiltered
concentrationconcentrated
customto afford an oil that
customwas purified by chromatography on silica gel eluting with ethyl acetate/iso-hexane mixtures

Sources & evidence

ORD record: ord-5c9d21a427214b9897378043c920c7d3
Source dataset: uspto-grants-2010_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07662825B2

Reaction notes

Loading…