Diethyl Ether → N-[2-chloro-5-(1-hydroxy-1-methyl-ethyl)-phenyl]-3,4-dimethoxy-benzenesulfonamide

HRID 1674631Notes

Reaction equation

[C:1]([C:4]1[CH:5]=[CH:6][C:7]([Cl:24])=[C:8]([NH:10][S:11]([C:14]2[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[C:16]([O:22][CH3:23])[CH:15]=2)(=[O:13])=[O:12])[CH:9]=1)(=[O:3])[CH3:2].C[Li].[CH3:27]COCC>C1COCC1>[Cl:24][C:7]1[CH:6]=[CH:5][C:4]([C:1]([OH:3])([CH3:27])[CH3:2])=[CH:9][C:8]=1[NH:10][S:11]([C:14]1[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[C:16]([O:22][CH3:23])[CH:15]=1)(=[O:13])=[O:12]

Participants

Conditions

Temperature: -78 °C

Procedure

To a solution of N-(5-acetyl-2-chloro-phenyl)-3,4-dimethoxy-benzenesulfonamide (1.4 g, 3.8 mmol) in THF (16 mL) at −78° C. was added dropwise a solution of methyl lithium in ether (1.6 M, 6.5 mL, 2.75 eq). The mixture was stirred at −78° C. for 30 min and then allowed to warm to RT. The mixture was partitioned between EA and NH4Cl solution, the aqueous phase was once more extracted with EA and the combined organic layers were dried over MgSO4 and concentrated. The residue was purified by chromatography on SiO2 (hex/EA 2:1, 1:1) to give the desired product (0.97 g, 67%) as a yellowish foam.

Workup

temperatureto warm to RT
customThe mixture was partitioned between EA and NH4Cl solution
extractionthe aqueous phase was once more extracted with EA
dry with materialthe combined organic layers were dried over MgSO4
concentrationconcentrated
customThe residue was purified by chromatography on SiO2 (hex/EA 2:1, 1:1)

Sources & evidence

ORD record: ord-724e8131a59c4e38bed2cb1e209151f3
Source dataset: uspto-grants-2011_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08003654B2

Reaction notes

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