Water → HCID 178466001, compound

HRID 2399361Notes

Reaction equation

HRID 2399361 reaction equation
[NH2:1][C:2]1[N:3]=[N:4][C:5]([C:8]2[CH:13]=[CH:12][C:11]([O:14][CH:15]([F:17])[F:16])=[C:10]([O:18][CH2:19][CH3:20])[CH:9]=2)=[CH:6][CH:7]=1.ClC1C=C(C=CC=1)C(OO)=[O:26].O>C(O)(=O)C>[NH2:1][C:2]1[N+:3]([O-:26])=[N:4][C:5]([C:8]2[CH:13]=[CH:12][C:11]([O:14][CH:15]([F:16])[F:17])=[C:10]([O:18][CH2:19][CH3:20])[CH:9]=2)=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 962WaterHCID 70297m-Chloroperbenzoic acidHCID 19385482HCID 19385482, compound

Product 1

HCID 178466001HCID 178466001, compoundYield 60.7%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
60 °C

Procedure

8.9 g (31.6 mmol) of 3-amino-6-(4-difluoromethoxy-3-ethoxyphenyl)pyridazine in 60 ml of glacial acetic acid are heated with 10.9 g (63.2 mmol) of m-chloroperoxybenzoic acid with stirring at 60° C. for 2 h. After cooling, the solution is stirred into 100 ml of water, the solution is exhaustively extracted with ethyl acetate, and the organic extract is dried over magnesium sulfate, concentrated in vacuo and chromatographed on neutral silica gel first with ethyl acetate and then with ethyl acetate/methanol 8:2. The appropriate fractions are concentrated, the residue is taken up in a little ethyl acetate, petroleum ether (b.p. 40°-70° C.) is added to incipient opalescence, and the product is crystallized by cooling. The crystals are filtered off with suction, washed with petroleum ether and dried at 80° C. in vacuo. 5.7 g (60.7%) of the title compound of m.p. 202°-3° C. are obtained.

Workup

  1. temperatureAfter cooling
  2. extractionthe solution is exhaustively extracted with ethyl acetate
  3. extractionthe organic extract
  4. dry with materialis dried over magnesium sulfate
  5. concentrationconcentrated in vacuo
  6. customchromatographed on neutral silica gel first with ethyl acetate
  7. concentrationThe appropriate fractions are concentrated
  8. additionis added to incipient opalescence
  9. customthe product is crystallized
  10. temperatureby cooling
  11. filtrationThe crystals are filtered off with suction
  12. washwashed with petroleum ether
  13. customdried at 80° C. in vacuo

Sources & evidence

ORD record
ord-f7c8b243cd3742e2aedbf53e7f7de127
Source dataset
uspto-grants-1995_09
Patent number
US05449676

Reaction notes

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