Water → 2-(1H-Tetrazol-1-YL)benzonitrile

HRID 1795262Notes

Reaction equation

HRID 1795262 reaction equation
[N:1]1([C:6]2[CH:14]=[CH:13][CH:12]=[CH:11][C:7]=2[C:8]([NH2:10])=O)[CH:5]=[N:4][N:3]=[N:2]1.[OH-].COC(NS([NH3+])(=O)=O)=O.O>O1CCCC1>[N:1]1([C:6]2[CH:14]=[CH:13][CH:12]=[CH:11][C:7]=2[C:8]#[N:10])[CH:5]=[N:4][N:3]=[N:2]1

Participants

5

Reactant 3

HCID 962WaterHCID 8559562-(1H-Tetrazol-1-YL)benzamideHCID 21866229(Methoxycarbonylsulfamoyl)ammonium hydroxide

Product 1

HCID 218662732-(1H-Tetrazol-1-YL)benzonitrile

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 2-tetrazol-1-yl-benzamide (1.5 g, 7.9 mmol) in tetrahydrofuran (50 ml) was added (methoxycarbonylsulfamoyl)ammonium hydroxide, inner salt (2.8 g, 11.8 mmol) in three portions over 1.5 h. Water was added and the reaction mixture was extracted with ethyl acetate. The combined organic layers were washed with brine. Drying and solvent evaporation gave 2-tetrazol-1-yl-benzonitrile; 1H NMR (CDCl3, 400 MHz) δ 9.27 (s, 1H), 7.90 (m, 3H), 7.72 (m, 1H).

Workup

  1. extractionthe reaction mixture was extracted with ethyl acetate
  2. washThe combined organic layers were washed with brine
  3. customDrying
  4. customsolvent evaporation

Sources & evidence

ORD record
ord-d3bb02b339414d488e0a204054e12d78
Source dataset
uspto-grants-2006_04
Patent number
US07026324B2

Reaction notes

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