Hydroxyamine hydrochloride → HCID 85073502, compound

HRID 226167Notes

Reaction equation

HRID 226167 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][CH:22]=[CH:21][C:20]=2[CH:25]=[CH:26][C:27](Cl)=[O:28])(=[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:20]1[CH:21]=[CH:22][CH:23]=[CH:24][C:19]=1[S:16](=[O:18])(=[O:17])[NH:15][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1

Participants

5

Reactant 3

HCID 443297Hydroxyamine hydrochlorideHCID 516892Sodium BicarbonateHCID 73989419HCID 73989419, compound

Product 1

HCID 85073502HCID 85073502, compoundYield 30%

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-(2-phenylsulfamoyl-phenyl)-acryloyl chloride (36a) (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 and crystallised from acetonitrile to give the title compound (0.056 g, 30%) as white crystals, m.p. 205-206.5° C. 1H NMR (DMSO-d6, HMDSO), δ: 6.37 (1H, d, J=16.0 Hz); 6.99-8.04 (10H, m); 8.23 (1H, d, J=16.0 Hz); 10.55 (1H, s), 10.83 (1H, br s). HPLC analysis on Symmetry C18 column: impurities 6.4% (column size 3.9×150 mm; mobile phase acetonitrile—0.1M phosphate buffer, pH 2.5, 30:70; sample concentration 0.2 mg/ml; flow rate 1.2 ml/min; detector UV 220 nm). Anal. Calcd for C15H14N2O4S*0.1 H2O, %: C 56.28, H 8.75, N 4.47. Found, %: C 55.63, H 9.07, N 4.36.

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
  6. customcrystallised from acetonitrile

Sources & evidence

ORD record
ord-6f6b6a8084ec466aaa2cde1a4e3301dd
Source dataset
uspto-grants-2009_07
Patent number
US07557140B2

Reaction notes

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