Phosphorus oxychloride → HCID 20080518, compound

HRID 1653824Notes

Reaction equation

HRID 1653824 reaction equation
P(Cl)(Cl)(Cl)=O.[C:6]1([C:12](=[O:32])[CH:13]([C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[NH:14][C:15](=O)[CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH:21]([C:23]#[N:24])[CH3:22])[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1>C1(C)C=CC=CC=1>[C:26]1([C:13]2[N:14]=[C:15]([CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH:21]([CH3:22])[C:23]#[N:24])[O:32][C:12]=2[C:6]2[CH:7]=[CH:8][CH:9]=[CH:10][CH:11]=2)[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=1

Participants

4

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 20080542HCID 20080542, compound

Product 1

HCID 20080518HCID 20080518, compoundYield 76.9%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
80 °C

Procedure

7.3 g of phosphorus oxychloride are added to a solution of 5.75 g of (RS)-1,2-diphenyl-2-(7-cyanooctanamido)ethanone in 30 cm3 of toluene, and the mixture is heated to 80° C. for 6 hours. After treatment, the product obtained is chromatographed on a column 2 cm in diameter containing 60 g of silica gel (50 to 200μ). The column is eluted with 0.6 liter of diisopropyl ether, collecting 50 cm3 fractions. The fractions emerging at between 0.1 liter and 0.6 liter are concentrated under reduced pressure (0.2 kPa). 4.2 g (76%) of (RS)-7-(4,5-diphenyl-2-oxazolyl)-2-methylheptanenitrile are obtained in the form of an oil, which is used directly in the subsequent reaction.

Workup

  1. customAfter treatment, the product obtained
  2. customis chromatographed on a column 2 cm in diameter
  3. additioncontaining 60 g of silica gel (50 to 200μ)
  4. washThe column is eluted with 0.6 liter of diisopropyl ether
  5. customcollecting 50 cm3 fractions
  6. concentrationare concentrated under reduced pressure (0.2 kPa)

Sources & evidence

ORD record
ord-7d6541a0dcc043b99c0e9ac1e1a5013b
Source dataset
uspto-grants-1995_04
Patent number
US05403852

Reaction notes

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