Ammonium Chloride → 5-((4-bromophenyl)methyl)-1H-1,2,3,4-tetrazole

HRID 1647056Notes

Reaction equation

HRID 1647056 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9]#[N:10])=[CH:4][CH:3]=1.[N-:11]=[N+:12]=[N-:13].[Na+].[Cl-].[NH4+]>CN(C=O)C>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9]2[N:11]=[N:12][NH:13][N:10]=2)=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 27914Benzeneacetonitrile, 4-bromo-HCID 33557Sodium Azide

Product 1

HCID 148887005-((4-bromophenyl)methyl)-1H-1,2,3,4-tetrazoleYield 46.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

4-Bromophenylacetonitrile (30.0 g, 0.15 mol), sodium azide (10.9 g, 0.17 mol) and ammonium chloride (8.9 g, 0.17 mol) were heated in DMF (300 mL) at 90° C. for 2 days. After concentration, water (200 mL) was added to the residue, the mixture was basified with 1M NaOH (170 mL) and washed with ether (2×100 mL). Acidification of the aqueous layer with 1N HCl and collection of the precipitate by suction filtration produced the crude product. This was purified by recrystallization from ethanol to provide 5-[(4-bromophenyl)methyl]-2H-tetrazole (17.2 g, 0.07 mol) in 44% yield, mp. 173°-175° C.

Workup

  1. concentrationAfter concentration, water (200 mL)
  2. additionwas added to the residue
  3. washwashed with ether (2×100 mL)
  4. customAcidification of the aqueous layer with 1N HCl and collection of the precipitate
  5. filtrationby suction filtration
  6. customproduced the crude product
  7. customThis was purified by recrystallization from ethanol

Sources & evidence

ORD record
ord-fd2b58de4c6741fd8a98e55e5e274558
Source dataset
uspto-grants-1993_01
Patent number
US05182263

Reaction notes

Loading…