Sodium Azide → methyl 3-(1-(2-cyanoethyl)-1H-tetrazol-5-yl)benzoate

HRID 1455366Notes

Reaction equation

HRID 1455366 reaction equation
[C:1]([CH2:3][CH2:4][NH:5][C:6]([C:8]1[CH:9]=[C:10]([CH:15]=[CH:16][CH:17]=1)[C:11]([O:13][CH3:14])=[O:12])=O)#[N:2].[N-:18]=[N+:19]=[N-:20].[Na+].O(S(C(F)(F)F)(=O)=O)S(C(F)(F)F)(=O)=O.C([O-])(O)=O.[Na+]>CC#N.CCOC(C)=O>[C:1]([CH2:3][CH2:4][N:5]1[C:6]([C:8]2[CH:9]=[C:10]([CH:15]=[CH:16][CH:17]=2)[C:11]([O:13][CH3:14])=[O:12])=[N:20][N:19]=[N:18]1)#[N:2]

Participants

7

Reactant 4

HCID 33557Sodium AzideHCID 67749Trifluoromethanesulfonic anhydrideHCID 516892Sodium BicarbonateHCID 21075152Methyl 3-((2-cyanoethyl)carbamoyl)benzoate

Product 1

HCID 21075151methyl 3-(1-(2-cyanoethyl)-1H-tetrazol-5-yl)benzoateYield 41.2%

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 8857Ethyl AcetateSolvent

Procedure

Preparation H7, Step 2: To a soultion of methyl 3-((2-cyanoethyl)carbamoyl)benzoate (400 mg, 1.7 mmol) in MeCN (15 mL) at 0° C. was added NaN3 (111 mg, 1.7 mmol), and Tf2O (0.3 mL, 1.7 mmol). The mixture was stirred at rt for 16 h before aq NaHCO3 and EtOAc were added. The organic layer was separated and re-washed twice before it was collected, dried over Na2SO4, and concentrated to methyl 3-(1-(2-cyanoethyl)-1H-tetrazol-5-yl)benzoate as an oil (180 mg, 41% yield). MS found: (M+H)+=258.

Workup

  1. customPreparation H7, Step 2
  2. additionwere added
  3. customThe organic layer was separated
  4. washre-washed twice before it
  5. customwas collected
  6. dry with materialdried over Na2SO4

Sources & evidence

ORD record
ord-f9980501fcc74be4961646443400c887
Source dataset
uspto-grants-2009_01
Patent number
US07482335B2

Reaction notes

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