Acetonitrile → HCID 21075154, compound

HRID 1171497Notes

Reaction equation

HRID 1171497 reaction equation
[C:1]([C:5]1[CH:6]=C([CH:11]=[C:12]([C:14](=O)[NH:15]CCC#N)[CH:13]=1)C([O-])=O)([CH3:4])([CH3:3])[CH3:2].[N-:21]=[N+:22]=[N-:23].[Na+].[C:25]([O-])(O)=O.[Na+].C[CH2:31][O:32][C:33]([CH3:35])=[O:34].[CH3:36][C:37]#[N:38]>>[C:1]([C:5]1[CH:6]=[C:35]([CH:11]=[C:12]([C:14]2[N:21]=[N:22][N:23]([CH2:25][CH2:36][C:37]#[N:38])[N:15]=2)[CH:13]=1)[C:33]([O:32][CH3:31])=[O:34])([CH3:2])([CH3:3])[CH3:4]

Participants

6

Reactant 5

HCID 6342AcetonitrileHCID 8857Ethyl AcetateHCID 33557Sodium AzideHCID 516892Sodium BicarbonateHCID 21075075HCID 21075075, compound

Product 1

HCID 21075154HCID 21075154, compoundYield 80%

Procedure

To a solution of 3-tert-butyl-5-((2-cyanoethyl)carbamoyl)benzoat (520 mg, 1.8 mmol) in MeCN (15 mL) at 0° C. was added NaN3 (117 mg, 1.8 mmol), and Tf20 (0.3 mL, 1.8 mm01). 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-tert-butyl-5-(2-(2-cyanoethyl)-2H-tetrazol-5-yl)benzoate as an oil (450 mg, 80% yield). MS found: (M+H)+=314.

Workup

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

Sources & evidence

ORD record
ord-fbdac88cae45497caf9d1080db93fab5
Source dataset
uspto-grants-2010_11
Patent number
US07829571B2

Reaction notes

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