Silicon tetrachloride → 4'-Methyl-5-(5-methyl-tetrazol-1-yl)-biphenyl-3-carboxylic acid methyl ester

HRID 736901Notes

Reaction equation

HRID 736901 reaction equation
Cl[Si](Cl)(Cl)Cl.[N-:6]=[N+:7]=[N-:8].[Na+].[CH3:10][O:11][C:12]([C:14]1[CH:15]=[C:16]([C:24]2[CH:29]=[CH:28][C:27]([CH3:30])=[CH:26][CH:25]=2)[CH:17]=[C:18]([NH:20][C:21](=O)[CH3:22])[CH:19]=1)=[O:13]>C(#N)C>[CH3:10][O:11][C:12]([C:14]1[CH:15]=[C:16]([C:24]2[CH:29]=[CH:28][C:27]([CH3:30])=[CH:26][CH:25]=2)[CH:17]=[C:18]([N:20]2[C:21]([CH3:22])=[N:8][N:7]=[N:6]2)[CH:19]=1)=[O:13]

Participants

5

Reactant 3

HCID 24816Silicon tetrachlorideHCID 33557Sodium AzideHCID 578514405-Acetylamino-4'-methyl-biphenyl-3-carboxylic acid methyl ester

Product 1

HCID 578509314'-Methyl-5-(5-methyl-tetrazol-1-yl)-biphenyl-3-carboxylic acid methyl esterYield 85%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of tetrachlorosilane (10.07 mmol, 2 mL), NaN3 (30.21 mmol, 1.96 g) and 5-acetylamino-4′-methyl-biphenyl-3-carboxylic acid methyl ester (3.36 mmol, 950.9 mg) in 10 ml of dry acetonitrile was stirred at room temperature for 16 hours. The reaction mixture were poured into ice-cold aqueous Na2CO3 solution and extracted with ethyl acetate (100 mL). The organic layer was washed with brine, dried over anhydrous Na2SO4, filtered, and concentrated in vacuo. The resulting crude 4′-methyl-5-(5-methyl-tetrazol-1-yl)-biphenyl-3-carboxylic acid methyl ester was used for next step directly (880 mg, 85% yield).

Workup

  1. additionThe reaction mixture were poured into ice-cold aqueous Na2CO3 solution
  2. extractionextracted with ethyl acetate (100 mL)
  3. washThe organic layer was washed with brine
  4. dry with materialdried over anhydrous Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-6cf9e632bc124aefa80133d4ac4ca13b
Source dataset
uspto-grants-2009_09
Patent number
US07595405B2

Reaction notes

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