Dabco → 6-(3,5-Dichloro-4-methylphenyl)-3-morpholinocarbonyloxypyridazine

HRID 1277938Notes

Reaction equation

HRID 1277938 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:10]2[CH:11]=[CH:12][C:13](=[O:16])[NH:14][N:15]=2)[CH:5]=[C:6]([Cl:9])[C:7]=1[CH3:8].C1N2CCN(CC2)C1.[O:25]1[CH2:30][CH2:29][N:28]([C:31](Cl)=[O:32])[CH2:27][CH2:26]1>CN(C)P(=O)(N(C)C)N(C)C>[Cl:1][C:2]1[CH:3]=[C:4]([C:10]2[N:15]=[N:14][C:13]([O:16][C:31]([N:28]3[CH2:29][CH2:30][O:25][CH2:26][CH2:27]3)=[O:32])=[CH:12][CH:11]=2)[CH:5]=[C:6]([Cl:9])[C:7]=1[CH3:8]

Participants

5

Reactant 3

HCID 9237DabcoHCID 848104-Morpholinecarbonyl chlorideHCID 93341Diclomezine

Product 1

HCID 128891056-(3,5-Dichloro-4-methylphenyl)-3-morpholinocarbonyloxypyridazineYield 95.5%

Reagents, catalysts & solvents 1

HCID 12679HexamethylphosphoramideSolvent

Procedure

1.27 g of 6-(3,5-dichloro-4-methylphenyl)-3-pyridazone and 1.12 g of triethylenediamine were dissolved in 25 ml of hexamethylphosphoric triamide, and then 1.5 g of morpholinocarbonyl chloride were added dropwise thereto. When the addition was complete, the mixture was stirred at room temperature for 1 hour and then poured into about 200 g of ice-water. The precipitate thus produced was collected by filtration, washed with water and dried, giving 1.75 g (94%) of the desired Compound No. 10. The melting point and spectroscopic data of this product agreed completely with those of the product obtained in Example 2.

Workup

  1. additionWhen the addition
  2. customThe precipitate thus produced
  3. filtrationwas collected by filtration
  4. washwashed with water
  5. customdried

Sources & evidence

ORD record
ord-ead66e59dc8842d39ca865a2e3eb93e5
Source dataset
uspto-grants-1981_07
Patent number
US04279908

Reaction notes

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