Phosphorus pentachloride → HCID 54498860, compound

HRID 439728Notes

Reaction equation

HRID 439728 reaction equation
[C:1]([C:4]([NH:9][C:10]([C:12]1[C:20]([C:21]([O:23][CH3:24])=[O:22])=[CH:19][CH:18]=[C:17]2[C:13]=1[C:14]([CH3:26])=[N:15][N:16]2[CH3:25])=O)([CH3:8])[CH:5]([CH3:7])[CH3:6])(=[O:3])[NH2:2].P(Cl)(Cl)(Cl)(Cl)Cl.C(=O)(O)[O-].[Na+]>C1(C)C=CC=CC=1>[CH:5]([C:4]1([CH3:8])[C:1](=[O:3])[NH:2][C:10]([C:12]2[C:20]([C:21]([O:23][CH3:24])=[O:22])=[CH:19][CH:18]=[C:17]3[C:13]=2[C:14]([CH3:26])=[N:15][N:16]3[CH3:25])=[N:9]1)([CH3:7])[CH3:6]

Participants

5

Reactant 3

HCID 24819Phosphorus pentachlorideHCID 516892Sodium BicarbonateHCID 22402960HCID 22402960, compound

Product 1

HCID 54498860HCID 54498860, compoundYield 85.7%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
90 °C

Procedure

A mixture of methyl 4-[(1-carbamoyl-1,2-dimethylpropyl)carbamoyl]-1,3-dimethyl-1H-indazole-5-carboxylate (0.600 g, 1.67 mmol), phosphorus pentachloride (1.04 g, 5.00 mmol) and dry toluene (7.0 mL) is stirred for 3.5 hours at 90° C. cooled and filtered. The filter cake is washed with toluene, slurried in water, treated with sodium bicarbonate (0.370 g, 4.40 mmol) to pH 8.5 and filtered to afford the title product as a white solid (0.490 g, 85.7%), mp 130°-150° C.

Workup

  1. temperaturecooled
  2. filtrationfiltered
  3. washThe filter cake is washed with toluene
  4. filtrationfiltered

Sources & evidence

ORD record
ord-d0901a4ec9e543439a73381fa380e031
Source dataset
uspto-grants-1996_05
Patent number
US05516751

Reaction notes

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