Phosphorus oxychloride → HCID 73679007, compound

HRID 1979520Notes

Reaction equation

HRID 1979520 reaction equation
[S:1]([C:5]1[CH:14]=[CH:13][C:12]([NH:15][N:16]=[C:17]([C:20]([CH3:22])=[O:21])[C:18]#[N:19])=[C:11]2[C:6]=1[CH:7]=[CH:8][CH:9]=[N:10]2)(O)(=[O:3])=[O:2].[K].P(Cl)(Cl)([Cl:26])=O>CN1CCCC1=O>[Cl:26][S:1]([C:5]1[CH:14]=[CH:13][C:12]([NH:15][N:16]=[C:17]([C:20]([CH3:22])=[O:21])[C:18]#[N:19])=[C:11]2[C:6]=1[CH:7]=[CH:8][CH:9]=[N:10]2)(=[O:3])=[O:2]

Participants

5

Reactant 3

HCID 24813Phosphorus oxychlorideHCID 5462222PotassiumHCID 73679006HCID 73679006, compound

Product 1

HCID 73679007HCID 73679007, compound

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

To a 250 ml round-bottom flask fitted with calcium sulfate drying tube was added 4.5 g (0.0126 m) of 2-(5-sulfo-8-quinolylhydrazono)acetoacetonitrile, potassium salt and 45 ml phosphorus oxychloride. The resultant slurry was chilled to <5° C. and 4.5 ml N-methylpyrrolidinone was slowly added. After stirring 1 hour. at 0°-5° C., the slurry was stirred overnight at room temperature followed by quenching in 500 ml ice water. The resultant yellow solid was collected, air dried and recrystallized from 100 ml acetonitrile. Yield 3.0 g yellow needles (70 percent).

Workup

  1. customTo a 250 ml round-bottom flask fitted with calcium sulfate drying tube
  2. temperatureThe resultant slurry was chilled to <5° C.
  3. stirringat 0°-5° C., the slurry was stirred overnight at room temperature
  4. customby quenching in 500 ml ice water
  5. customThe resultant yellow solid was collected
  6. customair dried
  7. customrecrystallized from 100 ml acetonitrile

Sources & evidence

ORD record
ord-c968df59692d4d91bed554b4228b19ee
Source dataset
uspto-grants-1984_11
Patent number
US04481141

Reaction notes

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