Dimethylformamide → 5-(2-Bromophenyl)-1H-tetrazole

HRID 1386671Notes

Reaction equation

HRID 1386671 reaction equation
[Br:1][C:2]1[CH:9]=[CH:8][C:5](C#N)=[CH:4][CH:3]=1.[N-:10]=[N+:11]=[N-:12].[Na+].[NH4+].[Cl-].C[N:17]([CH:19]=O)C>>[Br:1][C:2]1[CH:9]=[CH:8][CH:5]=[CH:4][C:3]=1[C:19]1[NH:17][N:12]=[N:11][N:10]=1

Participants

5

Reactant 4

HCID 6228DimethylformamideHCID 12162Benzonitrile, 4-bromo-HCID 25517Ammonium ChlorideHCID 33557Sodium Azide

Product 1

HCID 1784193735-(2-Bromophenyl)-1H-tetrazoleYield 58%

Conditions

Temperature
100 °C

Procedure

A mixture of 546 mg (3.0 mmol) of 4-(bromo)benzonitrile, 227 mg (3.5 mmol) of sodium azide and 187 mg (3.5 mmol) of NH4Cl in 5 mL of DMF was stirred at 100° C. for 20 h. The mixture was cooled and concentrated. The residue was dissolved in 20 mL of H2O and the pH adjusted to 2 with 2 N HCl solution. The solid that precipitated was filtered, rinsed with H2O, then ether and dried to afford 395 mg (58%) of the title compound: El-MS 226+224 (20%, M+H), 198+196 (100%, M−N2+H).

Workup

  1. temperatureThe mixture was cooled
  2. concentrationconcentrated
  3. dissolutionThe residue was dissolved in 20 mL of H2O
  4. customThe solid that precipitated
  5. filtrationwas filtered
  6. washrinsed with H2O
  7. dry with materialether and dried

Sources & evidence

ORD record
ord-926829d4cc96426fb249fe34311afdd2
Source dataset
uspto-grants-2001_07
Patent number
US06265434B1

Reaction notes

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