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

HRID 1674629Notes

Reaction equation

HRID 1674629 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]=[O:9])=[CH:4][C:3]=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].C[Li].[CH3:26]COCC>C1COCC1>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([OH:9])[CH3:26])=[CH:4][C:3]=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

5

Reactant 3

HCID 3283Diethyl EtherHCID 57511304N-(2-chloro-5-formyl-phenyl)-3,4-dimethoxy-benzenesulfonamideHCID 178418348HCID 178418348, compound

Product 1

HCID 57511305N-[2-chloro-5-(1-hydroxy-ethyl)-phenyl]-3,4-dimethoxy-benzenesulfonamideYield 100%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-78 °C

Procedure

To a solution of N-(2-chloro-5-formyl-phenyl)-3,4-dimethoxy-benzenesulfonamide (1.77 g, 5 mmol) in THF (20 mL) at −78° C. was added dropwise a solution of methyl lithium in ether (1.6 M, 8.6 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 dried under hv to give the desired product (1.8 g, 100%) as a yellowish oil.

Workup

  1. temperatureto warm to RT
  2. customThe mixture was partitioned between EA and NH4Cl solution
  3. extractionthe aqueous phase was once more extracted with EA
  4. dry with materialthe combined organic layers were dried over MgSO4
  5. concentrationconcentrated
  6. customThe residue was dried under hv

Sources & evidence

ORD record
ord-e0194d3c5ab441e29dd0851840870840
Source dataset
uspto-grants-2011_08
Patent number
US08003654B2

Reaction notes

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