Sodium Azide → 3-(4-Azido-naphthalen-1-yl)-5-(3,5-dichloro-phenyl)-5-trifluoromethyl-4,5-dihydro-isoxazole

HRID 388377Notes

Reaction equation

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

Participants

Conditions

Temperature: 80 °C

Procedure

Sodium azide (3.3 g) is added to a solution of 5-(3,5-dichloro-phenyl)-3-(4-fluoro-naphthalen-1-yl)-5-trifluoromethyl-4,5-dihydro-isoxazole (10.7 g) in DMF (50 ml). After 20 hours at 80° C. another portion of sodium azide is added (3.3 g) and the reaction mixture is stirred for 20 hours at 80° C. The solution is cooled to room temperature and the volume concentrated to 10 ml in vacuo. Water and ethyl acetate are added and the precipitate is collected after filtration to yield 3-(4-azido-naphthalen-1-yl)-5-(3,5-dichloro-phenyl)-5-trifluoromethyl-4,5-dihydro-isoxazole as a beige solid: 183-185° C.

Workup

temperatureThe solution is cooled to room temperature
concentrationthe volume concentrated to 10 ml in vacuo
additionWater and ethyl acetate are added
customthe precipitate is collected
filtrationafter filtration

Sources & evidence

ORD record: ord-0c941a55257c4888af9ed0e59ee787b2
Source dataset: uspto-grants-2013_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08377942B2

Reaction notes

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