Sodium Azide → HCID 22385625, compound

HRID 895127Notes

Reaction equation

N([O-])=O.[Na+].[F:5][C:6]1[CH:7]=[C:8]([NH2:19])[CH:9]=[C:10]([F:18])[C:11]=1[N:12]1[CH2:17][CH2:16][O:15][CH2:14][CH2:13]1.[N-:20]=[N+:21]=[N-].[Na+].C([O-])(=O)C.[Na+]>Cl>[N:19]([C:8]1[CH:7]=[C:6]([F:5])[C:11]([N:12]2[CH2:13][CH2:14][O:15][CH2:16][CH2:17]2)=[C:10]([F:18])[CH:9]=1)=[N+:20]=[N-:21]

Participants

Conditions

Temperature: 0 °C

Procedure

Sodium nitrite (0.91 g, 13.3 mmol) was added to an ice-cooled solution of 3,5-difluoro-4-morpholin-4-yl-phenylamine (0.95 g, 4.4 mmol), obtained in Preparation 6, in 6N HCl (30 mL) and the resulting yellow solution was stirred at 0° C. for 2 h. To this mixture was added an aqueous solution containing sodium azide (0.575 g, 8.86 mmol) and sodium acetate (57.5 g, 88.6 mmol). The reaction mixture was then extracted with ethyl acetate (50 mL×2) and the combined extracts were washed with 5% sodium bicarbonate solution followed by brine and dried over sodium sulfate. Evaporation of volatiles yielded the title compound as brown solid (1 g, 96%).

Workup

additionTo this mixture was added an aqueous solution
extractionThe reaction mixture was then extracted with ethyl acetate (50 mL×2)
washthe combined extracts were washed with 5% sodium bicarbonate solution
dry with materialdried over sodium sulfate
customEvaporation of volatiles

Sources & evidence

ORD record: ord-fd79eaff8e764164a8fbc41aa1995229
Source dataset: uspto-grants-2005_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06914058B2

Reaction notes

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