Phosphorus oxychloride → HCID 20080503, compound

HRID 1653818Notes

Reaction equation

HRID 1653818 reaction equation
P(Cl)(Cl)(Cl)=O.[CH3:6][O:7][C:8]1[CH:13]=[CH:12][C:11]([C:14](=O)[CH:15]([C:28]2[CH:33]=[CH:32][C:31]([O:34][CH3:35])=[CH:30][CH:29]=2)[NH:16][C:17](=[O:27])[CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH:23]([C:25]#[N:26])[CH3:24])=[CH:10][CH:9]=1>C1(C)C=CC=CC=1>[CH3:35][O:34][C:31]1[CH:32]=[CH:33][C:28]([C:15]2[N:16]=[C:17]([CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH:23]([CH3:24])[C:25]#[N:26])[O:27][C:14]=2[C:11]2[CH:10]=[CH:9][C:8]([O:7][CH3:6])=[CH:13][CH:12]=2)=[CH:29][CH:30]=1

Participants

4

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 20080505HCID 20080505, compound

Product 1

HCID 20080503HCID 20080503, compoundYield 93.9%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
80 °C

Procedure

15 g of phosphorus oxychloride is added with stirring to a solution of 13.8 g of (RS)-1,2-bis(4-methoxyphenyl)-2-(7-cyanooctanamido)ethanone in 65 cm3 of toluene, and the mixture is heated to 80° C. for 4 hours. The solution is poured onto 50 g of ice, the toluene phase is separated after settling has taken place and the aqueous phase is extracted with twice 50 cm3 of ethyl acetate. The combined organic extracts are washed with water (3 times 20 cm3) and with 30 cm3 of saturated aqueous sodium chloride solution. After drying over-sodium sulphate, the solvent is evaporated off under reduced pressure. The residue is chromatographed on a column 2.8 cm in diameter containing 100 g of silica gel (50 to 200). The column is eluted, collecting 50 cm3 fractions, with 1.8 liters of diisopropyl ether. The fractions emerging at between 0.3 liter and 1.8 liters are concentrated under reduced pressure (0.2 kPa). 12.4 g (93%) of (RS)-7-[4,5-bis(4-methoxyphenyl)-2-oxazolyl]-2-methylheptanenitrile are obtained in the form of a yellowish oil, which is used directly in the subsequent reaction.

Workup

  1. customthe toluene phase is separated after settling
  2. extractionthe aqueous phase is extracted with twice 50 cm3 of ethyl acetate
  3. washThe combined organic extracts are washed with water (3 times 20 cm3) and with 30 cm3 of saturated aqueous sodium chloride solution
  4. dry with materialAfter drying over-sodium sulphate
  5. customthe solvent is evaporated off under reduced pressure
  6. customThe residue is chromatographed on a column 2.8 cm in diameter
  7. additioncontaining 100 g of silica gel (50 to 200)
  8. washThe column is eluted
  9. customcollecting 50 cm3 fractions
  10. concentrationare concentrated under reduced pressure (0.2 kPa)

Sources & evidence

ORD record
ord-306455f54164436e9577f60b4568c806
Source dataset
uspto-grants-1995_04
Patent number
US05403852

Reaction notes

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