Hydrochloric Acid → Methyl 5-(tetrazol-5-yl)biphenyl-3-carboxylate

HRID 1096952Notes

Reaction equation

HRID 1096952 reaction equation
[N-:1]=[N+:2]=[N-:3].[Na+].Cl.C(N(CC)CC)C.[C:13]([C:15]1[CH:16]=[C:17]([C:27]([O:29][CH3:30])=[O:28])[CH:18]=[C:19]([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[CH:20]=1)#[N:14].Cl>CN(C=O)C>[NH:1]1[C:13]([C:15]2[CH:16]=[C:17]([C:27]([O:29][CH3:30])=[O:28])[CH:18]=[C:19]([C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)[CH:20]=2)=[N:14][N:3]=[N:2]1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 11130Triethylamine hydrochlorideHCID 33557Sodium AzideHCID 57346364Methyl 5-cyano-[1,1'-biphenyl]-3-carboxylate

Product 1

HCID 178497260Methyl 5-(tetrazol-5-yl)biphenyl-3-carboxylate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

Sodium azide (880 mg) and triethylamine hydrochloride (1.9 g) were added to a DMF (40 mL) solution of methyl 5-cyanobiphenyl-3-carboxylate (1.09 g), and stirred at 100° C. for 9 hours. With cooling with ice, diluted hydrochloric acid was added to it, the formed precipitate was taken out through filtration, washed with water, and dried to obtain the title compound as a white powder.

Workup

  1. additionwas added to it
  2. filtrationthe formed precipitate was taken out through filtration
  3. washwashed with water
  4. customdried

Sources & evidence

ORD record
ord-624b9471f1da4ca598e4564e5ceafbcb
Source dataset
uspto-grants-2012_03
Patent number
US08138197B2

Reaction notes

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