Phosphorus trichloride → HCID 15906515, compound

HRID 1358788Notes

Reaction equation

HRID 1358788 reaction equation
O[CH:2]([NH:7][C:8](=[O:16])[C:9]1[CH:14]=[CH:13][C:12]([Cl:15])=[CH:11][CH:10]=1)[C:3]([F:6])([F:5])[F:4].P(Cl)(Cl)[Cl:18]>P(Cl)(Cl)(Cl)=O.CCCCCCC>[Cl:18][CH:2]([NH:7][C:8](=[O:16])[C:9]1[CH:14]=[CH:13][C:12]([Cl:15])=[CH:11][CH:10]=1)[C:3]([F:6])([F:5])[F:4]

Participants

5

Reactant 2

HCID 24387Phosphorus trichlorideHCID 113227584-chloro-N-(2,2,2-trifluoro-1-hydroxyethyl)benzamide

Product 1

HCID 15906515HCID 15906515, compoundYield 89.3%

Reagents, catalysts & solvents 2

HCID 8900HeptaneSolventHCID 24813Phosphorus oxychlorideSolvent

Procedure

A mixture of N-(1-hydroxy-2,2,2-trifluoroethyl)-4-chlorobenzamide (2.53 g, 0.01 mol) in phosphorus oxychloride (2 mL) is treated with phosphorus trichloride (1.57 g, 0.012 mol), heated to and held at 80° C. for 30 minutes, and concentrated in vacuo to obtain a residue. The residue is dissolved in hot heptane, decanted from the waxy phosphorus products, and crystallized to give the title product as a white crystalline solid (2.43 g, 89.3% yield): mp 119.0-121.0° C.; IR (Nujol) 3266, 1668 cm−1; 1H NMR (CDCl3) δ7.76 and 7.46 (AB with fine splitting, ArH), 6.86 (d, J=8.5 Hz, NH, moves to 10.24 in DMSO-d6), 6.55(m, CH); 19F NMR δ−77.7(d, J=5 Hz).

Workup

  1. temperatureheated to and
  2. concentrationconcentrated in vacuo
  3. customto obtain a residue
  4. customdecanted from the waxy phosphorus products
  5. customcrystallized

Sources & evidence

ORD record
ord-3f3bff3ff6974fe7bb1c51be54c797b4
Source dataset
uspto-grants-2003_07
Patent number
US06596902B2

Reaction notes

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