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

HRID 487801Notes

Reaction equation

HRID 487801 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°-1750C.

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-94d24b62ab254b47b5758c97b6e6e730
Source dataset
uspto-grants-1994_03
Patent number
US05296608

Reaction notes

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