Hydrochloric Acid → HCID 178435521, compound

HRID 2211374Notes

Reaction equation

[CH3:1][C:2]([C:33]#[N:34])([CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][O:9][C:10]1[CH:15]=[C:14]([O:16][CH2:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[C:13]([C:24]2[CH:29]=[CH:28][C:27]([F:30])=[CH:26][CH:25]=2)=[CH:12][C:11]=1[CH2:31][CH3:32])[CH3:3].Cl.C(N(CC)CC)C.[N-:43]=[N+:44]=[N-:45].[Na+].Cl>CN(C)C=O.O>[CH3:1][C:2]([C:33]1[NH:45][N:44]=[N:43][N:34]=1)([CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][O:9][C:10]1[CH:15]=[C:14]([O:16][CH2:17][C:18]2[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=2)[C:13]([C:24]2[CH:29]=[CH:28][C:27]([F:30])=[CH:26][CH:25]=2)=[CH:12][C:11]=1[CH2:31][CH3:32])[CH3:3]

Participants

Conditions

Temperature: 125 °C

Procedure

A mixture of 1.44 g of 2-methyl-2-cyano-7-(2-ethyl-4-(4-fluorophenyl)-5-benzyloxyphenoxy)heptane, 4.1 g of triethylamine hydrochloride, and 1.95 g of sodium azide in 40 mL of dimethylformamide was heated in an oil bath at 125° C. for 17 hours, adding an additional 4 g of triethylamine hydrochloride and 2 g of sodium azide after 5 hours. The mixture was cooled, diluted with water, acidified with 1.0N hydrochloric acid, and extracted with ethyl acetate. The organic phase was washed with water, washed with saturated sodium chloride, dried over sodium sulfate, and evaporated in vacuo. The residue was chromatographed on silica gel eluting with dichloromethane/methanol to provide 1.12 g (72%) of the desired title product. NMR.

Workup

temperatureThe mixture was cooled
extractionextracted with ethyl acetate
washThe organic phase was washed with water
washwashed with saturated sodium chloride
dry with materialdried over sodium sulfate
customevaporated in vacuo
customThe residue was chromatographed on silica gel eluting with dichloromethane/methanol

Sources & evidence

ORD record: ord-81474c6337be409fa0aba3301ea09ac6
Source dataset: uspto-grants-1995_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05462954

Reaction notes

Loading…