Ethyl Acetate → HCID 86657007, compound

HRID 1958841Notes

Reaction equation

[CH3:1][C:2]1[CH:18]=[CH:17][CH:16]=[C:15]([CH3:19])[C:3]=1[CH2:4][O:5][C:6]1[CH:7]=[C:8]([CH2:12]C#N)[CH:9]=[CH:10][CH:11]=1.[N-:20]=[N+:21]=[N-:22].[Na+].[Cl-].[NH4+:25].[C:26](OCC)(=O)C>CN(C)C=O.CCCCCC>[CH3:19][C:15]1[CH:16]=[CH:17][CH:18]=[C:2]([CH3:1])[C:3]=1[CH2:4][O:5][C:6]1[CH:7]=[C:8]([CH:9]=[CH:10][CH:11]=1)[CH2:12][N:25]1[CH:26]=[N:22][N:21]=[N:20]1

Participants

Conditions

Temperature: 90 °C

Procedure

A mixture of 2-(3-(2,6-Dimethylbenzyloxy)phenyl)acetonitrile (Step B, 3.2 g, 12.7 mmol), sodium azide (1.28 g, 16.7 mmol) and ammonium chloride (1.08 g, 20.2 mmol) in dry dimethylformamide (30 ml) was heated under argon at 90° C. for 9 hours or until all the starting material is consumed and the reaction mixture was concentrated under reduced pressure. The reaction mixture was taken in ethyl acetate and washed with water (2×), dried over Na2SO4, filtered, concentrated and purified by flash chromatography on a silica gel column (methylene chloride:methanol 9:1) to give the oily product. The oil was stirred with 1:2 ethyl acetate:hexane for 10 minutes, and solid was filtered to give product as a white solid.

Workup

customis consumed
concentrationthe reaction mixture was concentrated under reduced pressure
washwashed with water (2×)
dry with materialdried over Na2SO4
filtrationfiltered
concentrationconcentrated
custompurified by flash chromatography on a silica gel column (methylene chloride:methanol 9:1)
customto give the oily product
filtrationsolid was filtered
customto give product as a white solid

Sources & evidence

ORD record: ord-599cd1a7a38f436d9bffcff40066bcd8
Source dataset: uspto-grants-2013_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08410154B2

Reaction notes

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