Ethyl Acetate → HCID 178424788, compound

HRID 337246Notes

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:13]#[N:14])[CH:9]=[CH:10][CH:11]=1.[N-:20]=[N+:21]=[N-:22].[Na+].[Cl-].[NH4+].C(OCC)(=O)C>CN(C)C=O.CCCCCC>[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]([CH:9]=[CH:10][CH:11]=1)[CH2:12][C:13]1[NH:22][N:21]=[N:20][N:14]=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-4b1ff655f1d842e49b6902bc41ea4f07
Source dataset: uspto-grants-2014_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08889724B2

Reaction notes

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