4-Methoxybenzenesulfonyl chloride → N1-(cyclohexylmethoxy)-4-methoxy-1-benzenesulfonamide

HRID 1166473Notes

Reaction equation

HRID 1166473 reaction equation
[CH:1]1([CH2:7][O:8][N:9]2C(=O)C3C(=CC=CC=3)C2=O)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.NN.[CH3:22][O:23][C:24]1[CH:29]=[CH:28][C:27]([S:30](Cl)(=[O:32])=[O:31])=[CH:26][CH:25]=1.C(N(C(C)C)CC)(C)C>C1COCC1>[CH:1]1([CH2:7][O:8][NH:9][S:30]([C:27]2[CH:26]=[CH:25][C:24]([O:23][CH3:22])=[CH:29][CH:28]=2)(=[O:32])=[O:31])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1

Participants

6

Reactant 4

HCID 74014-Methoxybenzenesulfonyl chlorideHCID 9321HydrazineHCID 81531DiisopropylethylamineHCID 140744162-(cyclohexylmethoxy)-1H-isoindole-1,3(2H)-dione

Product 1

HCID 22997206N1-(cyclohexylmethoxy)-4-methoxy-1-benzenesulfonamideYield 89.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

2-(cyclohexylmethoxy)-1H-isoindole-1,3(2H)-dione (11.8 mmol, 3.05 g) was combined with hydrazine (12.9 mmol, 0.41 mL) in anhydrous THF (25 mL) under nitrogen. The reaction immediately formed a white suspension and was allowed to stir at room temperature for 48 hours. The suspension was filtered directly into a flask containing 4-methoxybenzenesulfonyl chloride (9.5 mmol, 1.97 g) and diisopropylethylamine (11.6 mmol, 2.03 mL) was added. After stirring at room temperature for 18 hours, the reaction was concentrated to a solid residue and partitioned between ethyl acetate and 1N HCl. The organic layer was separated and washed with a saturated aqueous solution of sodium bicarbonate, and brine, and dried over magnesium sulfate. The product was concentrated to a solid and purified by silica gel chromatography (2:1 hexanes/ethyl acetate) providing 2.55g (80%) of a yellow solid. H1-NMR (CDCl3): δ 7.81 (2H,d), 6.97 (2H,d), 6.78 (1H,s), 3.85 (3H,s), 3.75 (2H,d), 1.65-1.55 (6H,m), 1.25-1.07 (3H,m), 0.93-0.85 (2H,m).

Workup

  1. customThe reaction
  2. customimmediately formed a white suspension
  3. filtrationThe suspension was filtered directly into a flask
  4. additionwas added
  5. stirringAfter stirring at room temperature for 18 hours
  6. concentrationthe reaction was concentrated to a solid residue
  7. custompartitioned between ethyl acetate and 1N HCl
  8. customThe organic layer was separated
  9. washwashed with a saturated aqueous solution of sodium bicarbonate, and brine
  10. dry with materialdried over magnesium sulfate
  11. concentrationThe product was concentrated to a solid
  12. custompurified by silica gel chromatography (2:1 hexanes/ethyl acetate)

Sources & evidence

ORD record
ord-7f0270b6374c4c37833de3c826ab0906
Source dataset
uspto-grants-2003_09
Patent number
US06613743B2

Reaction notes

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