Sodium Azide → 1-(2-cyclopropyl-5-nitrophenyl)-5-(trifluoromethyl)-1H-tetrazole

HRID 710222Notes

Reaction equation

HRID 710222 reaction equation
[N-:1]=[N+:2]=[N-:3].[Na+].Cl/[C:6](=[N:11]\[C:12]1[CH:17]=[C:16]([N+:18]([O-:20])=[O:19])[CH:15]=[CH:14][C:13]=1[CH:21]1[CH2:23][CH2:22]1)/[C:7]([F:10])([F:9])[F:8]>C(#N)C>[CH:21]1([C:13]2[CH:14]=[CH:15][C:16]([N+:18]([O-:20])=[O:19])=[CH:17][C:12]=2[N:11]2[C:6]([C:7]([F:10])([F:9])[F:8])=[N:3][N:2]=[N:1]2)[CH2:23][CH2:22]1

Participants

4

Reactant 2

HCID 33557Sodium AzideHCID 178526513HCID 178526513, compound

Product 1

HCID 580657791-(2-cyclopropyl-5-nitrophenyl)-5-(trifluoromethyl)-1H-tetrazole

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of NaN3 (0.56 g, 8.57 mmol, 2.5 eq) and (Z)—N-(1-chloro-2,2,2-trifluoroethylidene)-2-cyclopropyl-5-nitrobenzenamine intermediate (1.0 g, 3.43 mmol, 1.0 eq) in 15 mL dry acetonitrile was stirred at room temperature for 16 hours. The reaction mixture was poured into ice-cold aqueous Na2CO3 solution, extracted with ethyl acetate. The organic layer washed with brine, dried over Na2SO4, filtered, and concentrated in vacuo. The resulting crude mixture was purified by column chromatography, eluting with n-hexane: ethyl acetate (10-50% EtOAc in increments of 10% EtOAc)), giving the desired product in 37% overall yield (1.55 g).

Workup

  1. additionThe reaction mixture was poured into ice-cold aqueous Na2CO3 solution
  2. extractionextracted with ethyl acetate
  3. washThe organic layer washed with brine
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe resulting crude mixture was purified by column chromatography
  8. washeluting with n-hexane

Sources & evidence

ORD record
ord-9adf6f84115145aebec305c1904e4376
Source dataset
uspto-grants-2015_11
Patent number
US09181222B2

Reaction notes

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