Sodium Azide → 4'-Methyl-5-(5-trifluoromethyl-tetrazol-1-yl)-biphenyl-3-carboxylic acid methyl ester

HRID 736897Notes

Reaction equation

HRID 736897 reaction equation
[N-:1]=[N+:2]=[N-:3].[Na+].[CH3:5][O:6][C:7]([C:9]1[CH:10]=[C:11]([C:22]2[CH:27]=[CH:26][C:25]([CH3:28])=[CH:24][CH:23]=2)[CH:12]=[C:13](/[N:15]=[C:16](\Cl)/[C:17]([F:20])([F:19])[F:18])[CH:14]=1)=[O:8]>C(#N)C>[CH3:5][O:6][C:7]([C:9]1[CH:10]=[C:11]([C:22]2[CH:27]=[CH:26][C:25]([CH3:28])=[CH:24][CH:23]=2)[CH:12]=[C:13]([N:15]2[C:16]([C:17]([F:20])([F:19])[F:18])=[N:3][N:2]=[N:1]2)[CH:14]=1)=[O:8]

Participants

4

Reactant 2

HCID 33557Sodium AzideHCID 178498421HCID 178498421, compound

Product 1

HCID 578516694'-Methyl-5-(5-trifluoromethyl-tetrazol-1-yl)-biphenyl-3-carboxylic acid methyl esterYield 100%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of NaN3 (481 mg, 7.4 mmol) and 5-[1-chloro-2,2,2-trifluoro-eth-(Z)-ylideneamino]-4′-methyl-biphenyl-3-carboxylic acid methyl ester (1.3 g, 3.7 mmol) in 10 ml of dry ACN was stirred at room temperature for 16 hours. The reaction mixture were poured into ice-cold aqueous Na2CO3 solution, extracted with ethyl acetate. The organic layer washed with brine, dried over anhydrous Na2SO4, filtered, and concentrated in vacuo. The resulting crude 4′-methyl-5-(5-trifluoromethyl-tetrazol-1-yl)-biphenyl-3-carboxylic acid methyl ester (1.34 g, 99% yield) was used directly in the next step.

Workup

  1. additionThe reaction mixture were poured into ice-cold aqueous Na2CO3 solution
  2. extractionextracted with ethyl acetate
  3. washThe organic layer washed with brine
  4. dry with materialdried over anhydrous Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-5da9e59f4bb24cb78ba63f8e93e9c2e8
Source dataset
uspto-grants-2009_09
Patent number
US07595405B2

Reaction notes

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