Pyridine → HCID 14327313, compound

HRID 329468Notes

Reaction equation

[N:1]1([CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][O:11][C:12]2[CH:28]=[CH:27][C:15]([O:16][CH2:17][CH2:18][CH2:19][CH2:20][C:21]([CH3:26])([CH3:25])[C:22]([NH2:24])=O)=[CH:14][CH:13]=2)[CH:5]=[CH:4][N:3]=[CH:2]1.N1C=CC=CC=1.P(Cl)(Cl)(Cl)(Cl)Cl.C(Cl)(Cl)Cl>ClCCl>[N:1]1([CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][O:11][C:12]2[CH:13]=[CH:14][C:15]([O:16][CH2:17][CH2:18][CH2:19][CH2:20][C:21]([CH3:25])([CH3:26])[C:22]#[N:24])=[CH:27][CH:28]=2)[CH:5]=[CH:4][N:3]=[CH:2]1

Participants

Conditions

Temperature: -20 °C

Procedure

To a solution of 0.97 g 6-[p-[5-(1-imidazolyl)pentyloxy]phenoxy]-2,2-dimethylhexanamide in 50 ml dichloromethane was added 0.94 ml pyridine, the solution was cooled down to -20° C., 1.57 g phosphorus pentachloride was added, and the resulting mixture was stirred to allow the temperature to rise to 15° C. over a period of about one hour. Chloroform (30 ml) and ice water (30 ml) were admixed in that order, and the organic layer was collected and washed with 5% aqueous solution of sodium bicarbonate until the pH of aqueous layer rose to 7.5 to 8.0 and then with saturated sodium chloride solution. After dehydration, the solvent was distilled off, and the residue was purified by silica gel column chromatography, affording 0.82 g of 6-[p-[5-(1-imidazolyl)pentyloxy]phenoxy]-2,2-dimethylhexane-nitrile.

Workup

customthe organic layer was collected
washwashed with 5% aqueous solution of sodium bicarbonate until the pH of aqueous layer
distillationAfter dehydration, the solvent was distilled off
customthe residue was purified by silica gel column chromatography

Sources & evidence

ORD record: ord-c3e8d18804db445281f0c48e3be54cbc
Source dataset: uspto-grants-1990_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04891432

Reaction notes

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