Diethyl Ether → HCID 86666724, compound

HRID 2401397Notes

Reaction equation

[H-].[Na+].[Cl:3][C:4]1[CH:9]=[CH:8][C:7]([C:10]2[C:16]3[CH:17]=[CH:18][CH:19]=[CH:20][C:15]=3[C:14]3[C:21]([CH3:24])=[N:22][O:23][C:13]=3[CH2:12][N:11]=2)=[CH:6][CH:5]=1.CC(C1C=C(C(C)C)C(S([N:40]=[N+:41]=[N-:42])(=O)=O)=C(C(C)C)C=1)C.CCOCC>CN(C=O)C>[N:40]([CH:12]1[N:11]=[C:10]([C:7]2[CH:8]=[CH:9][C:4]([Cl:3])=[CH:5][CH:6]=2)[C:16]2[CH:17]=[CH:18][CH:19]=[CH:20][C:15]=2[C:14]2[C:21]([CH3:24])=[N:22][O:23][C:13]1=2)=[N+:41]=[N-:42]

Participants

Conditions

Temperature: 0 °C

Procedure

To a round bottom flask was added sodium hydride (0.13 g, 3.3 mmol, 60% in mineral oil). The flask was then purged with nitrogen, DMF (10 mL) was then added and the flask was cooled to 0° C. 6-(4-chlorophenyl)-1-methyl-4H-benzo[c]isoxazolo[4,5-e]azepine (930 mg, 3.0 mmol) in DMF (5 mL) was added and the reaction was allowed to stir for 45 min. Trisyl azide (1.40 g, 4.5 mmol) in DMF (5 mL) was added and the reaction was mixed at 0° C. for 1 h. The reaction poured into ether (100 mL) and washed with brine (3×). The organic layer was dried over Na2SO4, filtered, concentrated to afford crude 4-azido-6-(4-chlorophenyl)-1-methyl-4H-benzo[c]isoxazolo[4,5-e]azepine, which was used directly in the following reaction. LC/MS m/z 350 [M+H]+.

Workup

customThe flask was then purged with nitrogen, DMF (10 mL)
additionwas then added
additionthe reaction was mixed at 0° C. for 1 h
washwashed with brine (3×)
dry with materialThe organic layer was dried over Na2SO4
filtrationfiltered
concentrationconcentrated

Sources & evidence

ORD record: ord-219c08214ca546dd91cebeb2f3ebf00a
Source dataset: uspto-grants-2014_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08796261B2

Reaction notes

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