Phosphorus oxychloride → HCID 16718582, compound

HRID 910130Notes

Reaction equation

HRID 910130 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:13]([CH3:14])=[N:12][NH:11][C:10](=O)[C:9]=2[C:16]2[N:17]=[C:18]([CH3:22])[S:19][C:20]=2[CH3:21])=[CH:4][CH:3]=1.P(Cl)(Cl)([Cl:25])=O>>[Cl:25][C:10]1[N:11]=[N:12][C:13]([CH3:14])=[C:8]([C:5]2[CH:6]=[CH:7][C:2]([Cl:1])=[CH:3][CH:4]=2)[C:9]=1[C:16]1[N:17]=[C:18]([CH3:22])[S:19][C:20]=1[CH3:21]

Participants

3

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 57743123HCID 57743123, compound

Product 1

HCID 16718582HCID 16718582, compound

Conditions

Temperature
110 °C

Procedure

0.40 g of 5-(4-chlorophenyl)-4-(2,5-dimethyl-4-thiazolyl)-6-methyl-2H-pyridazin-3-one and 2 ml of phosphorus oxychloride were mixed. The mixture was stirred for 1 hour on an oil bath of 110° C. The reaction mixture was allowed to cool to room temperature, then, concentrated under reduced pressure. To the resultant residue was added ethyl acetate and ice water. The mixture was stirred for about 5 minutes at room temperature, then, liquid-partitioned. The organic layer was washed with brine three times, and dried over anhydrous magnesium sulfate, then, concentrated under reduced pressure to obtain 0.40 g 3-chloro-5-(4-chlorophenyl)-4-(2,5-dimethyl-4-thiazolyl)-6-m ethylpyridazine (hereinafter, described as compound (1) of the present invention.).

Workup

  1. temperatureto cool to room temperature
  2. concentrationconcentrated under reduced pressure
  3. additionTo the resultant residue was added ethyl acetate and ice water
  4. stirringThe mixture was stirred for about 5 minutes at room temperature
  5. customliquid-partitioned
  6. washThe organic layer was washed with brine three times
  7. dry with materialdried over anhydrous magnesium sulfate
  8. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-1655e6a69da34e52a162bc6c64939700
Source dataset
uspto-grants-2011_09
Patent number
US08022073B2

Reaction notes

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