Sodium Carbonate → 5-(1-ethyl-1H-tetrazol-5-yl)-4'-methyl-biphenyl-3-carboxylic acid methyl ester

HRID 77769

Reaction equation

HRID 77769 reaction equation
[N-:1]=[N+:2]=[N-:3].[Na+].[CH3:5][O:6][C:7]([C:9]1[CH:10]=[C:11]([C:20]2[CH:25]=[CH:24][C:23]([CH3:26])=[CH:22][CH:21]=2)[CH:12]=[C:13]([C:15](=O)[NH:16][CH2:17][CH3:18])[CH:14]=1)=[O:8].[Si](Cl)(Cl)(Cl)Cl.C([O-])([O-])=O.[Na+].[Na+]>C(#N)C>[CH3:5][O:6][C:7]([C:9]1[CH:10]=[C:11]([C:20]2[CH:21]=[CH:22][C:23]([CH3:26])=[CH:24][CH:25]=2)[CH:12]=[C:13]([C:15]2[N:16]([CH2:17][CH3:18])[N:3]=[N:2][N:1]=2)[CH:14]=1)=[O:8]

Participants

6

Reactant 4

HCID 10340Sodium CarbonateHCID 24816Silicon tetrachlorideHCID 33557Sodium AzideHCID 578516275-Ethylcarbamoyl-4'-methyl-biphenyl-3-carboxylic acid methyl ester

Product 1

HCID 578516285-(1-ethyl-1H-tetrazol-5-yl)-4'-methyl-biphenyl-3-carboxylic acid methyl esterYield 89%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Sodium azide (145.8 mg, 16.2 mmol) was added into a solution of 5-ethylcarbamoyl-4′-methyl-biphenyl-3-carboxylic acid methyl ester (210 mg, 0.7 mmol) and SiCl4 (0.62 mL, 5.4 mmol) in dry acetonitrile (14 mL). After the reaction was stirred at room temperature for 24 hours, the reaction mixture was poured into cold saturated aqueous Na2CO3 solution. This mixture was extracted with ethyl acetate and dried with anhydrous Na2SO4. Solvent was removed under reduced pressure to afford 200 mgs of 5-(1-ethyl-1H-tetrazol-5-yl)-4′-methyl-biphenyl-3-carboxylic acid methyl ester (yield 89%). MS (M+H)=323.

Workup

  1. extractionThis mixture was extracted with ethyl acetate
  2. dry with materialdried with anhydrous Na2SO4
  3. customSolvent was removed under reduced pressure

Sources & evidence

ORD record
ord-3193015355bc45958989cfe392214e26
Source dataset
uspto-grants-2014_09
Patent number
US08841336B2

Linked notes

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