Phosphorus pentachloride → HCID 54498860, compound

HRID 259730Notes

Reaction equation

HRID 259730 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-ae17fab58ae440f2a81f5818e2bb1ce5
Source dataset
uspto-grants-1996_06
Patent number
US05523279

Reaction notes

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