Sodium Acetate → HCID 15981236, compound

HRID 271171Notes

Reaction equation

HRID 271171 reaction equation
C([O-])(=[O:3])C.[Na+].[Cl:6][C:7]1[CH:8]=[C:9]([NH:25][C:26](=[O:30])[C:27]([OH:29])=[O:28])[CH:10]=[C:11]([Cl:24])[C:12]=1[O:13][C:14]1[N:15]=[N:16][C:17](Cl)=[C:18]([CH:20]([CH3:22])[CH3:21])[CH:19]=1>C(O)(=O)C>[Cl:6][C:7]1[CH:8]=[C:9]([NH:25][C:26](=[O:30])[C:27]([OH:29])=[O:28])[CH:10]=[C:11]([Cl:24])[C:12]=1[O:13][C:14]1[CH:19]=[C:18]([CH:20]([CH3:22])[CH3:21])[C:17](=[O:3])[NH:16][N:15]=1

Participants

4

Reactant 2

HCID 517045Sodium AcetateHCID 59834439HCID 59834439, compound

Product 1

HCID 15981236HCID 15981236, compoundYield 56.1%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of glacial acetic acid (55 mL), sodium acetate (1.2 g, 14.7 mmol) and N-[3,5-dichloro-4-(6-chloro-5-isopropyl-pyridazin-3-yloxy)-phenyl]-oxalamic acid (28) (1.7 g, 4.2 mmol) was heated to 100° C. for 24 h. The reaction mixture was cooled to room temperature and was concentrated under vacuum. The resulting solid was diluted with water (50 mL). The mixture was made acidic to pH=3 by the addition of glacial acetic acid. The solids were filtered and rinsed well with water and dried on the funnel. The solid was slurried in 1:1:2 isopropyl acetate: methyl tert-butyl ether:hexanes (3 mL) and then was heated to reflux. The mixture was cooled and filtered. A slight amount of impurity was detected by TLC. The solid was slurried in isopropyl acetate (10 mL) and filtered. The resulting pure solid was dried under high vacuum for 24 h and then dried in a vacuum oven at 80° C. for 24 h to afford N-[3,5-dichloro-4-(5-isopropyl-6-oxo-1,6-dihydro-pyridazin-3-yloxy)-phenyl]-oxalamic acid (29) (0.91 g, 56%) as a white solid; EI(+)-HRMS m/z calcd for C15H13Cl2N3O5 (M+H) 386.0305, found 386.0308. Molecular Weight=386.1940; Exact Mass=385.0232

Workup

  1. temperatureThe reaction mixture was cooled to room temperature
  2. concentrationwas concentrated under vacuum
  3. additionThe resulting solid was diluted with water (50 mL)
  4. additionThe mixture was made acidic to pH=3 by the addition of glacial acetic acid
  5. filtrationThe solids were filtered
  6. washrinsed well with water
  7. customdried on the funnel
  8. temperaturemethyl tert-butyl ether:hexanes (3 mL) and then was heated to reflux
  9. temperatureThe mixture was cooled
  10. filtrationfiltered
  11. filtrationfiltered
  12. customThe resulting pure solid was dried under high vacuum for 24 h
  13. customdried in a vacuum oven at 80° C. for 24 h

Sources & evidence

ORD record
ord-02abce83dc42453992771db84dad89c3
Source dataset
uspto-grants-2008_11
Patent number
US07452882B2

Reaction notes

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