Chloromethyl Methyl Ether → N-(2-bromo-5-chloro-pyridin-3-yl)-4-chloro-N-methoxymethyl-3-methyl-benzenesulfonamide

HRID 1898031Notes

Reaction equation

HRID 1898031 reaction equation
[CH3:1][O:2][CH2:3]Cl.[Br:5][C:6]1[C:11]([NH:12][S:13]([C:16]2[CH:21]=[CH:20][C:19]([Cl:22])=[C:18]([CH3:23])[CH:17]=2)(=[O:15])=[O:14])=[CH:10][C:9]([Cl:24])=[CH:8][N:7]=1.C(=O)([O-])[O-].[K+].[K+]>C1COCC1>[Br:5][C:6]1[C:11]([N:12]([CH2:3][O:2][CH3:1])[S:13]([C:16]2[CH:21]=[CH:20][C:19]([Cl:22])=[C:18]([CH3:23])[CH:17]=2)(=[O:15])=[O:14])=[CH:10][C:9]([Cl:24])=[CH:8][N:7]=1

Participants

5

Reactant 3

HCID 7864Chloromethyl Methyl EtherHCID 11430Potassium CarbonateHCID 86606891N-(2-bromo-5-chloro-pyridin-3-yl)-4-chloro-3-methyl-benzenesulfonamide

Product 1

HCID 57942201N-(2-bromo-5-chloro-pyridin-3-yl)-4-chloro-N-methoxymethyl-3-methyl-benzenesulfonamide

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Methoxymethyl chloride (1.2 g, 14.3 mmol) was added dropwise to a mixture of N-(2-bromo-5-chloro-pyridin-3-yl)-4-chloro-3-methyl-benzenesulfonamide (5.0 g, 12.7 mmol) and potassium carbonate (3.2 g, 23.2 mmol) in THF (30 mL) at room temperature. After 5 h, the potassium salts were removed by vacuum filtration and the filtrate was concentrated under reduced pressure. The residual light yellow solid was chromatographed on silica gel using ethyl acetate-hexane to provide the N-(2-bromo-5-chloro-pyridin-3-yl)-4-chloro-N-methoxymethyl-3-methyl-benzenesulfonamide as white crystals. MS m/z 441.2 (M+H).

Workup

  1. customthe potassium salts were removed by vacuum filtration
  2. concentrationthe filtrate was concentrated under reduced pressure
  3. customThe residual light yellow solid was chromatographed on silica gel

Sources & evidence

ORD record
ord-f245fa5628c0425186a872553d6d5cf5
Source dataset
uspto-grants-2013_08
Patent number
US08519135B2

Reaction notes

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