Phosphorus oxychloride → HCID 20080546, compound

HRID 1653821Notes

Reaction equation

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

Participants

Conditions

Temperature: 90 °C

Procedure

8 g of phosphorus oxychloride are added with stirring to a solution of 7.5 g (RS)-1,2-bis(4-chlorophenyl)-2-(7-cyanooctanamido)ethanone in 35 cm3 of toluene, and the mixture is heated to 90° C. for 6 hours. After treatment, the product obtained is chromatographed on a column 2.8 cm in diameter containing 110 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 0.15 liter and 0.6 liter are concentrated under reduced pressure (0.2 kPa). 6.6 g (91%) of (RS)-7-[4,5-bis(4-chlorophenyl)-2-oxazolyl]-2-methylheptanenitrile are obtained in the form of a yellowish oil, which is used directly in the subsequent reaction.

Workup

customAfter treatment, the product obtained
customis chromatographed on a column 2.8 cm in diameter
additioncontaining 110 g of silica gel (50 to 200μ)
washThe column is eluted with 0.6 liter of diisopropyl ether
customcollecting 50 cm3 fractions
concentrationare concentrated under reduced pressure (0.2 kPa)

Sources & evidence

ORD record: ord-b6087a2fe30542d79e0f30a2088281f7
Source dataset: uspto-grants-1995_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05403852

Reaction notes

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