تفاعل #2286296

ord-80bff88c65254ce1b1b9e2da6630f0cc

معادلة التفاعل

CC(=O)[O-].[Na+]
sodium acetate
CC(C)c1cc(Oc2c(Cl)cc(CC(=O)O)cc2Cl)nnc1Cl
[3,5-dichloro-4-(6-chloro-5-isopropyl-pyridazin-3-yloxy)-phenyl]-acetic acid
CC(C)c1cc(Oc2c(Cl)cc(CC(=O)O)cc2Cl)nnc1Cl
[3,5-Dichloro-4-(6-chloro-5-isopropyl-pyridazin-3-yloxy)-phenyl]-acetic acid
CC(C)c1cc(Oc2c(Cl)cc(CC(=O)O)cc2Cl)n[nH]c1=O
[3,5-dichloro-4-(5-isopropyl-6-oxo-1,6-dihydro-pyridazin-3-yloxy)-phenyl]-acetic acid
المردود 65.0%
CC(C)c1cc(Oc2c(Cl)cc(CC(=O)O)cc2Cl)n[nH]c1=O
[3,5-Dichloro-4-(5-isopropyl-6-oxo-1,6-dihydro-pyridazin-3-yloxy)-phenyl]-acetic acid
المردود 65.0%

المذيبات

ظروف التفاعل

درجة الحرارة
125°CELSIUS
الظروف التفصيلية
See reaction.notes.procedure_details.

المعالجة

  1. 1
    درجة الحرارةThe reaction mixture was cooled to room temperature
  2. 2
    تركيزconcentrated
  3. 3
    workup.ADDITIONThe resulting residue was diluted with methylene chloride (200 mL)
  4. 4
    غسيلwas washed with water (150 mL)
  5. 5
    أخرىThe organic layer was separated
  6. 6
    workup.ADDITIONHexanes (3×200 mL) were added to the residue in portions
  7. 7
    تركيزsubsequently concentrated under vacuum
  8. 8
    workup.ADDITIONThe resulting semi-solid was diluted with a minimum amount of ether
  9. 9
    ترشيحThe resulting white solid was filtered
  10. 10
    غسيلwashed with cold ether
  11. 11
    أخرىdried under high vacuum overnight

الإجراء التجريبي

A mixture of glacial acetic acid (200 mL), sodium acetate (6.1 g, 74.4 mmol) and [3,5-dichloro-4-(6-chloro-5-isopropyl-pyridazin-3-yloxy)-phenyl]-acetic acid (18) (8.3 g, 21.96 mmol) was heated to 125° C. for 24 h. The reaction mixture was cooled to room temperature and concentrated. The resulting residue was diluted with methylene chloride (200 mL) and was washed with water (150 mL). The organic layer was separated. Hexanes (3×200 mL) were added to the residue in portions and then subsequently concentrated under vacuum. The resulting semi-solid was diluted with a minimum amount of ether, scratched, and slurried. The resulting white solid was filtered, washed with cold ether and dried under high vacuum overnight to afford [3,5-dichloro-4-(5-isopropyl-6-oxo-1,6-dihydro-pyridazin-3-yloxy)-phenyl]-acetic acid (19) (5.1 g, 65%) as a white solid; LRMS for C15H14Cl2N2O4 (M+) m/z=357. Molecular Weight=357.1958; Exact Mass=356.0331

المصدر

DOI: 10.6084/m9.figshare.5104873.v1براءة الاختراع: USRE046024E1uspto-grants-2016_06