Sodium Hydroxide → 3-(4-Benzenesulfonylaminophenyl)-N-hydroxyacrylamide

HRID 2180441Notes

Reaction equation

HRID 2180441 reaction equation
O1CCOCC1.Cl.[NH2:8][OH:9].[OH-].[Na+].C[O:13][C:14](=O)[CH:15]=[CH:16][C:17]1[CH:22]=[CH:21][C:20]([NH:23][S:24]([C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)(=[O:26])=[O:25])=[CH:19][CH:18]=1>O.CO>[C:27]1([S:24]([NH:23][C:20]2[CH:21]=[CH:22][C:17]([CH:16]=[CH:15][C:14]([NH:8][OH:9])=[O:13])=[CH:18][CH:19]=2)(=[O:26])=[O:25])[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1

Participants

7

Reactant 4

HCID 14798Sodium HydroxideHCID 312751,4-DioxaneHCID 443297Hydroxyamine hydrochlorideHCID 67019618HCID 67019618, compound

Product 1

HCID 41513-(4-Benzenesulfonylaminophenyl)-N-hydroxyacrylamideYield 31%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

To a mixture, consisting of dioxane (25 ml), methanol (3 ml), and water (1 ml), hydroxylamine hydrochloride (0.834 g, 12 mmol) and NaOH (0.960 g, 24 mmol) followed by 3-(4-benzenesulfonylamino-phenyl)-acrylic acid methyl ester (74) (1.735 g, 4.1 mmol)) were added. The resulting mixture was vigorously stirred at ambient temperature for 24 hours and evaporated under reduced pressure. The residue was mixed with warm (50° C.) water and filtered. The aqueous solution was acidified with hydrochloric acid to pH 4 and filtered. The precipitate was washed with water (2×10 ml), ethyl acetate (10 ml), and crystallised from acetonitrile (15 ml) to give title compound as a yellow solid (0.405 g, 31%). M.p. 189-191° C. 1H NMR (DMSO-d6, HMDSO) δ: 6.30 (d, 1H, J=15.8 Hz); 7.12 (d, 2H, J=8.6 Hz); 7.32 (d, 1H, J=15.8 Hz); 7.45 (d, 2H, J=8.4 Hz); 7.48-7.86 (6H, m); 9.01 (s, 1H); 10.56 (s, 1H); 10.72 (s, 1H). HPLC analysis on Zorbax SB-C18 column: impurities 1.8% (column size 4.6×150 mm; mobile phase acetonitrile—0.1% H3PO4, gradient from 30:70 to 100:0; sample concentration 1.0 mg/ml; detector UV 220 nm). Anal. Calcd for C15H14N2O4S, %: C, 56.59; H, 4.43; N, 8.80; S, 10.07. Found, %: C, 56.03; H, 4.24; N, 8.66; S, 10.02.

Workup

  1. additionwere added
  2. customevaporated under reduced pressure
  3. additionThe residue was mixed
  4. temperaturewith warm (50° C.) water
  5. filtrationfiltered
  6. filtrationfiltered
  7. washThe precipitate was washed with water (2×10 ml), ethyl acetate (10 ml)
  8. customcrystallised from acetonitrile (15 ml)

Sources & evidence

ORD record
ord-19d84f93b5ee41ba9ad389dc6ce33a99
Source dataset
uspto-grants-2005_05
Patent number
US06888027B2

Reaction notes

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