Phosphorus pentachloride → HCID 90311126, compound

HRID 927190Notes

Reaction equation

HRID 927190 reaction equation
P(Cl)(Cl)(Cl)(Cl)[Cl:2].[C:7]([C:9]1[CH:14]=[CH:13][C:12]([CH:15](NC(=O)OCC)[NH:16][C:17](=[O:21])OCC)=[CH:11][CH:10]=1)#[N:8]>C1C=CC=CC=1>[Cl:2][CH:15]([N:16]=[C:17]=[O:21])[C:12]1[CH:13]=[CH:14][C:9]([C:7]#[N:8])=[CH:10][CH:11]=1

Participants

4

Reactant 2

HCID 24819Phosphorus pentachlorideHCID 90327759HCID 90327759, compound2×

Product 1

HCID 90311126HCID 90311126, compound

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

Phosphorous pentachloride (83.3 g, 400 mmol) is added to a suspension of diethyl (4-cyanophenyl)methylenedicarbamate (intermediate 1, 53.0 g, 182 mmol) in benzene (200 mL) and the mixture is heated at reflux for 2 h. The benzene is evaporated and the mixture is then purified by distillation under reduced pressure. The first fraction (ca. 40° C., ca. 0.01 mbar) is discarded. The second fraction (ca. 110° C., ca. 0.6 mbar) is collected. Yield: 28.4 g; ESI mass spectrum: [M+MeOH−HCl+H]+=189; Retention time HPLC: 0.65 min (Z003_004).

Workup

  1. temperaturethe mixture is heated
  2. temperatureat reflux for 2 h
  3. customThe benzene is evaporated
  4. distillationthe mixture is then purified by distillation under reduced pressure
  5. customThe first fraction (ca. 40° C., ca. 0.01 mbar)
  6. customThe second fraction (ca. 110° C., ca. 0.6 mbar) is collected
  7. custom0.65 min (Z003_004)

Sources & evidence

ORD record
ord-526f1e043ef44d749dfb0dae12f04af2
Source dataset
uspto-grants-2016_03
Patent number
US09290459B1

Reaction notes

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