Hydrochloric Acid → HCID 178520398, compound

HRID 350616Notes

Reaction equation

HRID 350616 reaction equation
[C:1]([CH2:3][C:4]([NH:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)=[O:5])#[N:2].C([Sn]([N:26]=[N+:27]=[N-:28])(CCCC)CCCC)CCC.Cl>C1(C)C=CC=CC=1.CCOCC>[NH:26]1[C:1]([CH2:3][C:4]([NH:6][C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)=[O:5])=[N:2][N:28]=[N:27]1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 69296Acetamide, 2-cyano-N-phenyl-HCID 4984872Tributyltin azide

Product 1

HCID 178520398HCID 178520398, compoundYield 90.3%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 3283Diethyl EtherSolvent

Procedure

A solution of 2-cyano-acetanilide (0.801 g, 5.0 mmol) and tri-n-butyltin azide (2.05 mL, 7.5 mmol) in anhydrous toluene (10 mL) was heated at reflux for 48 hrs. The mixture was allowed to cool to room temperature and treated with 2.0 N HCl in Et2O (5.0 mL). The resulting precipate was collected by suction, washed with hexane and dried in vacuo to give 2-(1H-tetrazol-5-yl)acetanilide (0.917 g, 90%) as a white solid.

Workup

  1. temperatureat reflux for 48 hrs
  2. customThe resulting precipate was collected by suction
  3. washwashed with hexane
  4. customdried in vacuo

Sources & evidence

ORD record
ord-c70a5eba16b7425b8003797554719346
Source dataset
uspto-grants-2007_02
Patent number
US07183260B2

Reaction notes

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