Sodium Azide → HCID 90423520, compound

HRID 1050188Notes

Reaction equation

HRID 1050188 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([CH:9]=[C:10]([C:12]([F:15])([F:14])[F:13])[CH:11]=1)[C:7]#[N:8])([O-:3])=[O:2].[N-:16]=[N+:17]=[N-:18].[Na+]>CN(C=O)C>[N+:1]([C:4]1[CH:5]=[C:6]([C:7]2[N:16]=[N:17][NH:18][N:8]=2)[CH:9]=[C:10]([C:12]([F:13])([F:14])[F:15])[CH:11]=1)([O-:3])=[O:2]

Participants

4

Reactant 2

HCID 33557Sodium AzideHCID 107274333-Cyano-5-nitrobenzotrifluoride

Product 1

HCID 90423520HCID 90423520, compoundYield 40.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
120 °C

Procedure

To a mixture of 3-nitro-5-(trifluoromethyl)benzonitrile (400 mg, 1.851 mmol) in DMF (20 mL) was added sodium azide (361 mg, 5.55 mmol) at rt. The mixture was stirred at 120° C. overnight. LCMS showed the reaction was finished. The reaction was quenched by water. The mixture was extracted with EA (20 mL×3), washed with water, and concentrated to give 5-(3-nitro-5-(trifluoromethyl)phenyl)-2H-tetrazole (220 mg, 0.743 mmol, 40.1% yield): 1H NMR (400 MHz, DMSO-d6) δ 9.03 (s, 1H), 8.73 (s, 1H), 8.66 (s, 1H), 7.92 (s, 1H). ES-LCMS m/z 260 (M+H).

Workup

  1. customThe reaction was quenched by water
  2. extractionThe mixture was extracted with EA (20 mL×3)
  3. washwashed with water
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-1cb74f234e534b418754235ac22cd903
Source dataset
uspto-grants-2016_07
Patent number
US09382238B2

Reaction notes

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