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

HRID 217344Notes

Reaction equation

HRID 217344 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-66355999b94a4c2489d16af2f6e845bd
Source dataset
uspto-grants-2012_06
Patent number
US08193368B2

Reaction notes

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