4-Methoxybenzenesulfonyl chloride → N1-isobutoxy-4-methoxy-1-benzenesulfonamide

HRID 29167Notes

Reaction equation

HRID 29167 reaction equation
Cl.[CH2:2]([O:6][NH2:7])[CH:3]([CH3:5])[CH3:4].[CH3:8][O:9][C:10]1[CH:15]=[CH:14][C:13]([S:16](Cl)(=[O:18])=[O:17])=[CH:12][CH:11]=1.C(N(C(C)C)CC)(C)C>C1COCC1>[CH2:2]([O:6][NH:7][S:16]([C:13]1[CH:12]=[CH:11][C:10]([O:9][CH3:8])=[CH:15][CH:14]=1)(=[O:18])=[O:17])[CH:3]([CH3:5])[CH3:4]

Participants

5

Reactant 3

HCID 74014-Methoxybenzenesulfonyl chlorideHCID 81531DiisopropylethylamineHCID 12696238O-(2-Methylpropyl)hydroxylamine--hydrogen chloride (1/1)

Product 1

HCID 22997112N1-isobutoxy-4-methoxy-1-benzenesulfonamide

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Isobutoxyamine hydrochloride (7.96 mmol, 1.0 g), 4-methoxybenzenesulfonyl chloride (7.24 mmol, 1.5 g), diisopropylethylamine (18.09 mmol, 3.15 mL) and anhydrous THF (15 mL) were combined under nitrogen. The reaction stirred at room temperature for 15 hours. The reaction solution was concentrated to a white solid and partitioned between ethyl acetate and 1N HCl. The organic layer was separated and washed with saturated aqueous sodium bicarbonate and brine, dried over magnesium sulfate and concentrated under vacuum to yield an off-white colored solid. Rf: 0.5 (2:1 hexanes/ethyl acetate); H1-NMR (CDCl3): δ 7.84 (2H,d), 6.99 (2H,d), 6.81 (1H,s), 3.87 (3H,s), 3.74 (2H,d), 1.90 (1H, septet), 0.86 (6H,d).

Workup

  1. concentrationThe reaction solution was concentrated to a white solid
  2. custompartitioned between ethyl acetate and 1N HCl
  3. customThe organic layer was separated
  4. washwashed with saturated aqueous sodium bicarbonate and brine
  5. dry with materialdried over magnesium sulfate
  6. concentrationconcentrated under vacuum
  7. customto yield an off-white colored solid

Sources & evidence

ORD record
ord-b2b2d00c64f042cfb5c1a112fb547c0e
Source dataset
uspto-grants-2008_09
Patent number
US07419967B2

Reaction notes

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