Hydroxyamine hydrochloride → 2-(Hydroxyimino)-3-(4-phenylthiophen-2-yl)propanoic acid

HRID 1397215Notes

Reaction equation

HRID 1397215 reaction equation
[C:1]1([C:7]2[CH:8]=[C:9]([CH2:12][C:13](=S)[C:14]([OH:16])=[O:15])[S:10][CH:11]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.Cl.[NH2:19][OH:20]>[O-]CC.[Na+]>[OH:20][N:19]=[C:13]([CH2:12][C:9]1[S:10][CH:11]=[C:7]([C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)[CH:8]=1)[C:14]([OH:16])=[O:15]

Participants

4

Reactant 2

HCID 443297Hydroxyamine hydrochlorideHCID 866775883-(4-Phenylthiophen-2-yl)-2-thioxopropanoic acid

Product 1

HCID 866775892-(Hydroxyimino)-3-(4-phenylthiophen-2-yl)propanoic acidYield 90%

Reagents, catalysts & solvents 1

HCID 2723922Sodium ethoxideSolvent

Procedure

3-(4-Phenylthiophen-2-yl)-2-thioxopropanoic acid (0.9 g, 3.4 mmol), hydroxylamine hydrochloride (740 mg, 10.6 mmol), and an ethanolic solution sodium ethoxide [prepared from 0.4 g of sodium and 30 mL of absolute ethanol] was refluxed for 1.5 h. Solvent was removed under reduced pressure and the residue was diluted with water and acidified with 1.5N HCl to adjust the pH of the solution ˜3. The solid product was extracted with EtOAc. The organic layer was dried over anhydrous Na2SO4, then removal of the solvent under reduced pressure yielded 2-(hydroxyimino)-3-(4-phenylthiophen-2-yl)propanoic acid (0.8 g, yield 89%) as an off-white solid. 1H NMR (400 MHz, MeOD) δ 7.59-7.57 (m, 2H), 7.37-7.33 (m, 3H), 7.24-7.23 (m, 2H), 3.31 (s, 2H). MS (ESI) m/z: Calculated for C13H11NO3S: 262.05. found: 262.0 (M+H)+.

Workup

  1. customSolvent was removed under reduced pressure
  2. additionthe residue was diluted with water
  3. extractionThe solid product was extracted with EtOAc
  4. dry with materialThe organic layer was dried over anhydrous Na2SO4
  5. customremoval of the solvent under reduced pressure

Sources & evidence

ORD record
ord-8aa348a7d3944d9b91de0b3f0ae05967
Source dataset
uspto-grants-2014_12
Patent number
US08901156B2

Reaction notes

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