Phosphorus oxychloride → HCID 17780353, compound

HRID 2187659Notes

Reaction equation

HRID 2187659 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[NH:9][C:10]3[C:15]([CH:16]=2)=[CH:14][C:13]([O:17][C:18]([F:21])([F:20])[F:19])=[CH:12][CH:11]=3)=[CH:4][CH:3]=1.C([N:25]1[CH2:29][C:28](=O)[N:27]=[CH:26]1)(=O)C.P(Cl)(Cl)([Cl:33])=O>>[ClH:33].[NH:27]1[CH2:28][CH2:29][N:25]=[C:26]1[C:16]1[C:15]2[C:10](=[CH:11][CH:12]=[C:13]([O:17][C:18]([F:21])([F:19])[F:20])[CH:14]=2)[NH:9][C:8]=1[C:5]1[CH:4]=[CH:3][C:2]([CH3:1])=[CH:7][CH:6]=1

Participants

4

Reactant 3

HCID 24813Phosphorus oxychlorideHCID 18476298HCID 18476298, compoundHCID 22350258N-acetyl-2-imidazolinone

Product 1

HCID 17780353HCID 17780353, compound

Conditions

Temperature
60 °C

Procedure

380 mg (1.3 mmol) of the indole from Step A was heated with 210 mg (1.6 mmol) of N-acetyl-2-imidazolinone in 1.3 ml of neat phosphoryl chloride at 60° C. for 20 h. The excess of phosphoryl chloride was removed under reduced pressure, and the residue was dissolved in 2 ml of absolute ethanol and heated at 60° C. for 5 h. The mixture was cooled, and the crystalline precipitate collected by filtration, washed with ethanol, and dried in vacuo.

Workup

  1. customThe excess of phosphoryl chloride was removed under reduced pressure
  2. dissolutionthe residue was dissolved in 2 ml of absolute ethanol
  3. temperatureThe mixture was cooled
  4. filtrationthe crystalline precipitate collected by filtration
  5. washwashed with ethanol
  6. customdried in vacuo

Sources & evidence

ORD record
ord-84807a0a3561482eb676cd05de1762a2
Source dataset
uspto-grants-2002_06
Patent number
US06410562B1

Reaction notes

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