Phosphorus oxychloride → HCID 18693014, compound

HRID 1870924Notes

Reaction equation

HRID 1870924 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:20]=[CH:19][CH:18]=[CH:17][C:9]=2[C:10]([NH:12][NH:13][C:14]([NH2:16])=[O:15])=O)=[CH:4][CH:3]=1.P(Cl)(Cl)(Cl)=O>C1C=CC=CC=1>[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:20]=[CH:19][CH:18]=[CH:17][C:9]=2[CH:10]2[NH:12][NH:13][C:14](=[O:15])[NH:16]2)=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 18693018HCID 18693018, compound

Product 1

HCID 18693014HCID 18693014, compoundYield 79%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

1-[2-(4-Methylphenyl)benzoyl]semicarbazide (4.6 g) and phosphorus oxychloride (10.3 g) were suspended in benzene (100 ml), and the suspension was heated for 3 hours under reflux. The reaction mixture was concentrated to dryness under reduced pressure. To the residue was added water, and resulting crystalline precipitate was collected by filtration. Recrystallization from methanol afforded the title compound as colorless needles (3.4 g, 79%), m.p.245-246° C. (decomp.).

Workup

  1. temperaturethe suspension was heated for 3 hours
  2. temperatureunder reflux
  3. concentrationThe reaction mixture was concentrated to dryness under reduced pressure
  4. additionTo the residue was added water
  5. customresulting crystalline precipitate
  6. filtrationwas collected by filtration
  7. customRecrystallization from methanol

Sources & evidence

ORD record
ord-ca0d2837e7c2455796b5a60277946d22
Source dataset
uspto-grants-2000_08
Patent number
US06100252

Reaction notes

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