Acetic Acid → Acetic acid 2-[3,5-dichloro-4-(5-isopropyl-6-oxo-1,6-dihydro-pyridazin-3-yloxy)-phenyl]-ethyl ester

HRID 1157229Notes

Reaction equation

HRID 1157229 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH2:20][CH2:21][OH:22])[CH:5]=[C:6]([Cl:19])[C:7]=1[O:8][C:9]1[N:10]=[N:11][C:12](Cl)=[C:13]([CH:15]([CH3:17])[CH3:16])[CH:14]=1.[C:23]([O-])(=[O:25])[CH3:24].[Na+].C(O)(=[O:30])C>>[Cl:1][C:2]1[CH:3]=[C:4]([CH2:20][CH2:21][O:22][C:23](=[O:25])[CH3:24])[CH:5]=[C:6]([Cl:19])[C:7]=1[O:8][C:9]1[CH:14]=[C:13]([CH:15]([CH3:17])[CH3:16])[C:12](=[O:30])[NH:11][N:10]=1

Participants

4

Reactant 3

HCID 176Acetic AcidHCID 517045Sodium AcetateHCID 598345252-[3,5-Dichloro-4-(6-chloro-5-isopropyl-pyridazin-3-yloxy)-phenyl]-ethanol

Product 1

HCID 59834524Acetic acid 2-[3,5-dichloro-4-(5-isopropyl-6-oxo-1,6-dihydro-pyridazin-3-yloxy)-phenyl]-ethyl esterYield 100%

Conditions

Temperature
114 °C

Procedure

A solution of 2-[3,5-dichloro-4-(6-chloro-5-isopropyl-pyridazin-3-yloxy)-phenyl]-ethanol (17) (500 mg, 1.38 mmol) in glacial acetic acid (5 mL) was treated with sodium acetate (230 mg, 2.8 mmol) and heated to 114° C. for 24 h. At this time, the reaction mixture was cooled to room temperature and was concentrated under vacuum. The resulting residue was diluted with methylene chloride (25 mL) and was washed with water (10 mL). The organic layer was separated and was washed with a saturated aqueous sodium bicarbonate solution (10 mL). The waters layers were combined and extracted with methylene chloride (10 mL). The organic layers were combined and dried with sodium sulfate, filtered, concentrated and dried under high vacuum overnight to afford acetic acid 2-[3,5-dichloro-4-(5-isopropyl-6-oxo-1,6-dihydro-pyridazin-3-yloxy)-phenyl]-ethyl ester (34) (531 mg, 100%) as a white solid; LRMS for C17H18Cl2N2O4 (M+) m/z=385 Molecular Weight=385.2500; Exact Mass=384.0644

Workup

  1. temperatureAt this time, the reaction mixture was cooled to room temperature
  2. concentrationwas concentrated under vacuum
  3. additionThe resulting residue was diluted with methylene chloride (25 mL)
  4. washwas washed with water (10 mL)
  5. customThe organic layer was separated
  6. washwas washed with a saturated aqueous sodium bicarbonate solution (10 mL)
  7. extractionextracted with methylene chloride (10 mL)
  8. dry with materialdried with sodium sulfate
  9. filtrationfiltered
  10. concentrationconcentrated
  11. customdried under high vacuum overnight

Sources & evidence

ORD record
ord-5653e9ce0ee44a809c201560bcdd6e64
Source dataset
uspto-grants-2010_10
Patent number
US07807674B2

Reaction notes

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