3-Bromobenzonitrile → HCID 178419385, compound

HRID 384311Notes

Reaction equation

HRID 384311 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][CH:9]=1)[C:5]#[N:6].[Cl-].[NH4+].[N-:12]=[N+:13]=[N-:14].[Na+]>CN(C=O)C>[Br:1][C:2]1[CH:3]=[C:4]([C:5]2[NH:14][N:13]=[N:12][N:6]=2)[CH:7]=[CH:8][CH:9]=1

Participants

5

Reactant 3

HCID 233813-BromobenzonitrileHCID 25517Ammonium ChlorideHCID 33557Sodium Azide

Product 1

HCID 178419385HCID 178419385, compoundYield 102.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

3-Bromo-benzonitrile 8a (18.2 g, 0.1 mol) and ammonium chloride (5.9 g, 0.11 mol) were dissolved in 80 mL of N,N′-dimethylformamide followed by addition of sodium azide (7.16 g, 0.11 mol) under argon atmosphere. The reaction mixture was heated to 100° C. and reacted overnight. Then the mixture was cooled to 60° C. and concentrated under reduced pressure to remove N,N′-dimethylformamide. The residue was diluted with 100 mL of water and 4 mL of concentrated hydrochloric acid and stirred for 1 hour. The mixture was filtered and dried to obtain the title compound 5-(3-bromo-phenyl)-1H-tetrazole 8b (23 g) as a white solid.

Workup

  1. customreacted overnight
  2. temperatureThen the mixture was cooled to 60° C.
  3. concentrationconcentrated under reduced pressure
  4. customto remove N,N′-dimethylformamide
  5. additionThe residue was diluted with 100 mL of water and 4 mL of concentrated hydrochloric acid
  6. filtrationThe mixture was filtered
  7. customdried

Sources & evidence

ORD record
ord-c224e77c778e4859bf1839c2dbeacfa8
Source dataset
uspto-grants-2013_02
Patent number
US08367710B2

Reaction notes

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