Hydrochloric Acid → 3-(Hydroxymethyl)-N-isopropylbenzenesulfonamide

HRID 916817Notes

Reaction equation

HRID 916817 reaction equation
[H-].[Na+].[OH:3][CH2:4][C:5]1[CH:6]=[C:7]([S:11]([NH2:14])(=[O:13])=[O:12])[CH:8]=[CH:9][CH:10]=1.[CH:15](I)([CH3:17])[CH3:16].Cl>CN(C=O)C.O>[OH:3][CH2:4][C:5]1[CH:6]=[C:7]([S:11]([NH:14][CH:15]([CH3:17])[CH3:16])(=[O:12])=[O:13])[CH:8]=[CH:9][CH:10]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 6362Isopropyl iodide2×HCID 24758Sodium hydride2×HCID 231337993-(Hydroxymethyl)benzene-1-sulfonamide

Product 1

HCID 657518003-(Hydroxymethyl)-N-isopropylbenzenesulfonamide

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

Sodium hydride (60% oil dispersion, 0.177 g) was added to 3-hydroxymethylbenzenesulfonamide (0.77 g) with stirring in DMF (15 ml) under nitrogen at 21°. After 10 min, isopropyl iodide (0.45 ml) was added followed by a further 0.3 ml after 1 h. After an additional 2 h more isopropyl iodide (0.2 ml) was added. After 3 days more sodium hydride oil dispersion (0.08 g) was added. After another day, the solution was poured into water acidified with 2M hydrochloric acid and the product was extracted with ethyl acetate twice. The combined extracts were washed with brine and evaporated to an oil. This oil was loaded onto a column of silica gel (60 g) and the column was eluted successively with 30%, 50% and 70% ethyl acetate in 40-60 petroleum ether to give the title compound (0.527 g) LCMS RT=2.22 min.

Workup

  1. waitfollowed by a further 0.3 ml after 1 h
  2. waitAfter another day
  3. extractionthe product was extracted with ethyl acetate twice
  4. washThe combined extracts were washed with brine
  5. customevaporated to an oil
  6. washthe column was eluted successively with 30%, 50% and 70% ethyl acetate in 40-60 petroleum ether

Sources & evidence

ORD record
ord-06bcce8c9bcd4d5a942213219a9d34ec
Source dataset
uspto-grants-2007_09
Patent number
US07271197B2

Reaction notes

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