Sodium Azide → HCID 57770821, compound

HRID 1669882Notes

Reaction equation

[CH3:1][O:2][CH2:3][CH:4]([NH:6][C:7]([C:9]1[CH:10]=[C:11]([C:16]2[CH:21]=[CH:20][C:19]([CH3:22])=[CH:18][CH:17]=2)[CH:12]=[C:13]([NH2:15])[CH:14]=1)=[O:8])[CH3:5].N([O-])=O.[Na+].[N-:27]=[N+:28]=[N-].[Na+]>FC(F)(F)C(O)=O.O>[CH3:1][O:2][CH2:3][CH:4]([NH:6][C:7]([C:9]1[CH:10]=[C:11]([C:16]2[CH:17]=[CH:18][C:19]([CH3:22])=[CH:20][CH:21]=2)[CH:12]=[C:13]([N:15]=[N+:27]=[N-:28])[CH:14]=1)=[O:8])[CH3:5]

Participants

Conditions

Temperature: 0 °C

Procedure

To a solution of 5-amino-4′-methyl-biphenyl-3-carboxylic acid (2-methoxy-1-methyl-ethyl)-amide (500 mg, 1.68 mmol) in trifluoroacetic acid (10 mL) was added a solution of NaNO2 (21.47 mmol, 1.49 g) in water (10 mL) at 0° C. The mixture was stirred at 0° C. for 10 minutes and a solution of NaN3 (44.43 mmol, 2.89 g) in water (10 mL) was added. The solution was stirred at room temperature for 16 hours. Solvent was removed under reduced pressure and the residue was extracted with ethyl acetate, washed with saturated aqueous NaHCO3, brine, dried over anhydrous Na2SO4, filtered and concentrated in vacuo to give 5-azido-4′-methyl-biphenyl-3-carboxylic acid (2-methoxy-1-methyl-ethyl)-amide. (80%). MS (M+H)=325.

Workup

stirringThe solution was stirred at room temperature for 16 hours
customSolvent was removed under reduced pressure
extractionthe residue was extracted with ethyl acetate
washwashed with saturated aqueous NaHCO3, brine
dry with materialdried over anhydrous Na2SO4
filtrationfiltered
concentrationconcentrated in vacuo

Sources & evidence

ORD record: ord-8a9247ce9cea4091987a82ab007be594
Source dataset: uspto-grants-2011_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07989637B2

Reaction notes

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