Hydrochloric Acid → HCID 85074082, compound

HRID 2184764Notes

Reaction equation

HRID 2184764 reaction equation
[Cl:1][C:2]1[S:6][C:5]([C:7]2[CH:12]=[CH:11][C:10]([C:13](=O)[CH2:14][CH2:15][C:16]([OH:18])=[O:17])=[CH:9][CH:8]=2)=[CH:4][CH:3]=1.Cl.[NH2:21][OH:22].C(=O)([O-])[O-].[Na+].[Na+].Cl>C(O)C>[Cl:1][C:2]1[S:6][C:5]([C:7]2[CH:12]=[CH:11][C:10]([C:13](=[N:21][OH:22])[CH2:14][CH2:15][C:16]([OH:18])=[O:17])=[CH:9][CH:8]=2)=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 10340Sodium CarbonateHCID 443297Hydroxyamine hydrochlorideHCID 12043169HCID 12043169, compound

Product 1

HCID 85074082HCID 85074082, compoundYield 85.7%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A stirred mixture of 4-[4-(5-chloro-thiophen-2-yl)-phenyl]-4-oxo-butyric acid (0.065 g, 0.00022 mol), hydroxylamine hydrochloride (0.0181 g, 0.000260 mol), sodium carbonate (0.0280 g, 0.000260 mol), and absolute ethanol was refluxed under nitrogen for 17 hours and allowed to cool. The resulting suspension was stirred at room temperature for 2 days and filtered. The filtercake was dissolved in methanol (5 mL) and water (5 mL), and the solution was filtered to remove a small amount of fines. The filtrate was acidified with 1.0 M aqueous hydrochloric acid (0.24 mL, 0.00024 mol), and the resulting suspension was rotary evaporated to remove methanol. The resulting aqueous suspension was filtered, washed with water, and dried in vacuo to give 0.0584 g of 4-[4-(5-chloro-thiophen-2-yl)-phenyl]-4-hydroxyimino-butyric acid as a pale yellow solid; mp 172-174° C.

Workup

  1. temperaturewas refluxed under nitrogen for 17 hours
  2. temperatureto cool
  3. filtrationfiltered
  4. dissolutionThe filtercake was dissolved in methanol (5 mL)
  5. filtrationwater (5 mL), and the solution was filtered
  6. customto remove a small amount of fines
  7. customthe resulting suspension was rotary evaporated
  8. customto remove methanol
  9. filtrationThe resulting aqueous suspension was filtered
  10. washwashed with water
  11. customdried in vacuo

Sources & evidence

ORD record
ord-fffe887a42024f9bbda9c0ff8f122cb6
Source dataset
uspto-grants-2002_06
Patent number
US06399612B1

Reaction notes

Loading…