Hydroxyamine hydrochloride → HCID 85049509, compound

HRID 2180428Notes

Reaction equation

HRID 2180428 reaction equation
Cl.[NH2:2][OH:3].C([O-])(O)=O.[Na+].[C:9]1([NH:15][S:16]([C:19]2[CH:24]=[CH:23][C:22]([CH:25]=[CH:26][C:27](Cl)=[O:28])=[CH:21][CH:20]=2)(=[O:18])=[O:17])[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1>O1CCCC1>[OH:3][NH:2][C:27](=[O:28])[CH:26]=[CH:25][C:22]1[CH:23]=[CH:24][C:19]([S:16](=[O:18])(=[O:17])[NH:15][C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)=[CH:20][CH:21]=1

Participants

5

Reactant 3

HCID 443297Hydroxyamine hydrochlorideHCID 516892Sodium BicarbonateHCID 73989400HCID 73989400, compound

Product 1

HCID 85049509HCID 85049509, compoundYield 39.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a suspension of hydroxylamine hydrochloride (0.21 g, 3.01 mmol) in tetrahydrofuran (4.0 ml) a saturated NaHCO3 solution (2.6 ml) was added and the resultant mixture was stirred at ambient temperature for 25 min. To the reaction mixture a 3-(4-phenylsulfamoyl-phenyl)-acryloyl chloride (44a) (0.19 g, 0.59 mmol) solution in tetrahydrofuran (2.5 ml) was added and the mixture was stirred at ambient temperature for 2 hours. The reaction mixture was partitioned between ethyl acetate and 2N HCl. The organic layer was washed successively with water and saturated NaCl, and the solvent was removed. The residue was washed with diethyl ether to give the title compound (0.074 g, 39%) as white crystals, m.p. 176-177.5° C. 1H NMR (DMSO-d6, HMDSO), δ: 6.54 (1H, d, J=16.0 Hz); 6.96-7.32 (5H, m); 7.47 (1H, d, J=16.0 Hz); 7.76 (4H, s); 9.14 (1H, br s); 10.29 (1H, br s); 10.86 (1H, s). Anal. Calcd for C15H14N2O4S, %: C, 56.59; H, 4.43; N, 8.80. Found, %: 55.82; H, 4.38; N, 9.01.

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

Sources & evidence

ORD record
ord-cc39843eb58d4bdd8e35020bb8ef0b58
Source dataset
uspto-grants-2005_05
Patent number
US06888027B2

Reaction notes

Loading…