Sodium Azide → HCID 22385625, compound

HRID 1270340Notes

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-09f17fcbdc694f5ab68d1b666c7bca83
Source dataset: uspto-grants-2007_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07202254B2

Reaction notes

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