Dimethylformamide → HCID 178521934, compound

HRID 35019Notes

Reaction equation

[F:1][C:2]([F:22])([C:15]([F:21])([F:20])[C:16]([F:19])([F:18])[F:17])[C:3]([NH:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=1[CH2:12][C:13]#[N:14])=[O:4].[N-:23]=[N+:24]=[N-:25].[Na+].[Cl-].[NH4+].CN(C)C=O>O>[F:1][C:2]([F:22])([C:15]([F:20])([F:21])[C:16]([F:19])([F:18])[F:17])[C:3]([NH:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=1[CH2:12][C:13]1[NH:25][N:24]=[N:23][N:14]=1)=[O:4]

Participants

Conditions

Temperature: 130 °C

Procedure

A mixture of 2,2,3,3,4,4,4-heptafluoro-N-[2-(cyanomethyl)phenyl]butanamide (15 g), sodium azide (14.85 g), ammonium chloride (12.22 g) and dimethylformamide (200 mL) was heated in a 130° C. oil bath under a nitrogen atmosphere overnight. The reaction mixture was cooled to room temperature, water (100 mL) was added and the product was extracted with ethylacetate (3×200 mL). The combined extracts were dried over Na2SO4, filtered and concentrated with a rotary evaporator. The brown residue was purified by high pressure liquid chromatography to give a white solid. The solid was triturated with diethyl ether to give 3.2 g of the title compound, m.p. 117°-178° C.

Workup

temperatureThe reaction mixture was cooled to room temperature
extractionthe product was extracted with ethylacetate (3×200 mL)
dry with materialThe combined extracts were dried over Na2SO4
filtrationfiltered
concentrationconcentrated with a rotary evaporator
customThe brown residue was purified by high pressure liquid chromatography
customto give a white solid
customThe solid was triturated with diethyl ether

Sources & evidence

ORD record: ord-489ff135d4144224a5c45da6e8862ab0
Source dataset: uspto-grants-1988_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04764623

Reaction notes

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