Chloride → HCID 25190241, compound

HRID 2410625Notes

Reaction equation

HRID 2410625 reaction equation
[CH2:1]([O:3][C:4](=[O:18])[CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][C:15](O)=[O:16])[CH3:2].[Cl-].O=S(Cl)Cl.Cl.[NH2:25][OH:26]>C(Cl)(Cl)Cl.ClCCl.N1C=CC=CC=1.C(OCC)(=O)C>[OH:26][NH:25][C:15](=[O:16])[CH2:14][CH2:13][CH2:12][CH2:11][CH2:10][CH2:9][CH2:8][CH2:7][CH2:6][CH2:5][C:4]([O:3][CH2:1][CH3:2])=[O:18]

Participants

9

Reactant 4

HCID 312ChlorideHCID 24386Thionyl ChlorideHCID 443297Hydroxyamine hydrochlorideHCID 560435HCID 560435, compound

Product 1

HCID 25190241HCID 25190241, compoundYield 82%

Reagents, catalysts & solvents 4

HCID 1049PyridineSolventHCID 6212ChloroformSolventHCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

In a single-neck flask equipped with reflux condenser, under stirring and argon flux, the 12-ethoxy-12-oxododecanoic acid (13; 1.5 g, 5.8 mmol) is solved in chloroform (20 mL). Thionyle chloride is dropped (SOCl2; 0.64 mL, 8.8 mmol) and the reaction is carried on under reflux for 3 h. The mixture is cooled down to room temperature and the solvent is eliminated under high vacuum. The obtained product is solved in dichloromethane (20 mL) and is added, at room temperature and under stirring, with a solution of hydroxylamine hydrochloride (0.61 g, 8.8 mmol) in pyridine (10 mL) leaving to react for 12 h under the same conditions. All the solvent are eliminated under high vacuum and the remaining product is solubilised in ethyl acetate (50 mL), washed with distilled water (3×20 mL). The organic phase is anhydrified with anhydrous sodium sulphate and filtered under vacuum. The solvent is evaporated and dried under high vacuum to give 1.3 g (Yield=82%) of product as a pale yellow solid.

Workup

  1. customIn a single-neck flask equipped
  2. temperaturewith reflux condenser
  3. temperatureunder reflux for 3 h
  4. additionis added, at room temperature
  5. customleaving
  6. customto react for 12 h under the same conditions
  7. washwashed with distilled water (3×20 mL)
  8. filtrationfiltered under vacuum
  9. customThe solvent is evaporated
  10. customdried under high vacuum

Sources & evidence

ORD record
ord-dd5b592a288e439582a50d9f905114ae
Source dataset
uspto-grants-2014_08
Patent number
US08816107B2

Reaction notes

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