Hydroxyamine hydrochloride → N-Hydroxy-3-[3-(naphthalen-2-ylsulfamoyl)-phenyl]-acrylamide

HRID 351064Notes

Reaction equation

HRID 351064 reaction equation
Cl.[NH2:2][OH:3].C([O-])(O)=O.[Na+].[CH:9]1[C:18]2[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=2)[CH:12]=[CH:11][C:10]=1[NH:19][S:20]([C:23]1[CH:24]=[C:25]([CH:29]=[CH:30][C:31](Cl)=[O:32])[CH:26]=[CH:27][CH:28]=1)(=[O:22])=[O:21]>O1CCCC1>[OH:3][NH:2][C:31](=[O:32])[CH:30]=[CH:29][C:25]1[CH:26]=[CH:27][CH:28]=[C:23]([S:20](=[O:22])(=[O:21])[NH:19][C:10]2[CH:11]=[CH:12][C:13]3[C:18](=[CH:17][CH:16]=[CH:15][CH:14]=3)[CH:9]=2)[CH:24]=1

Participants

5

Reactant 3

HCID 443297Hydroxyamine hydrochlorideHCID 516892Sodium BicarbonateHCID 739894303-[3-(Naphthalen-2-ylsulfamoyl)phenyl]-acryloyl Chloride

Product 1

HCID 85040616N-Hydroxy-3-[3-(naphthalen-2-ylsulfamoyl)-phenyl]-acrylamideYield 68%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a suspension of hydroxylamine hydrochloride (0.2 g, 2.85 mmol) in tetrahydrofuran (3.5 ml) a saturated NaHCO3 solution (2.3 ml) was added and the resultant mixture was stirred at ambient temperature for 10 min. To the reaction mixture a solution of crude 3-[3-(naphthalen-2-ylsulfamoyl)-phenyl]-acryloyl chloride (16e) (0.21 g) in tetrahydrofuran (2.5 ml) was added and the mixture was stirred at ambient temperature for one hour. The reaction mixture was partitioned between ethyl acetate and 2N HCl. The organic layer was washed successively with water and saturated NaCl, then the solvent was removed. The residue was washed with diethyl ether and potroleum ether-ethyl acetate (3:1) affording the title compound (0.14 g, 68%). M.p. 164° C. 1H NMR (DMSO-d6, HMDSO) δ: 6.49 (1H, d, J=16.0 Hz); 7.16–7.89 (12H, m); 7.98 (1H, br s); 10.52 (1H, s); 10.76 (1H, br s). HPLC analysis on Symmetry C18 column: impurities 5% (column size 3.9×150 mm; mobile phase acetonitrile—0.1M phosphate buffer (pH 2.5), 50:50; sample concentration 0.5 mg/ml; flow rate 0.8 ml/min; detector UV 220 nm). Anal. Calcd for C19H16N2O4S, %: C, 61.94; H, 4.38; N, 7.60. Found, %: C, 61.44; H, 4.39; N, 7.48.

Workup

  1. additionwas added
  2. customThe reaction mixture was partitioned between ethyl acetate and 2N HCl
  3. washThe organic layer was washed successively with water and saturated NaCl
  4. customthe solvent was removed
  5. washThe residue was washed with diethyl ether and potroleum ether-ethyl acetate (3:1)

Sources & evidence

ORD record
ord-b4af50788c634633812dba61e3ea27a7
Source dataset
uspto-grants-2007_02
Patent number
US07183298B2

Reaction notes

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