4-Chlorobutyronitrile → HCID 178478461, compound

HRID 2351867Notes

Reaction equation

HRID 2351867 reaction equation
[Cl:1][CH2:2][CH2:3][CH2:4][C:5]#[N:6].[N-:7]=[N+:8]=[N-:9].[Na+].[Cl-].[NH4+].[OH-].[Na+]>CN(C)C=O>[Cl:1][CH2:2][CH2:3][CH2:4][C:5]1[NH:9][N:8]=[N:7][N:6]=1

Participants

6

Reactant 4

HCID 123364-ChlorobutyronitrileHCID 14798Sodium HydroxideHCID 25517Ammonium ChlorideHCID 33557Sodium Azide

Product 1

HCID 178478461HCID 178478461, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
140 °C

Procedure

A mixture of 3.5 g of 4-chlorobutyronitrile, 2.3 g of sodium azide and 1.9 g of ammonium chloride in 50 ml of dimethylformamide is stirred at 140° C. for 20 hours. The reaction mixture is poured onto ice, basified with 1N sodium hydroxide and extracted twice with ethyl acetate. The aqueous fraction is acidified with acetic acid and extracted with ethylacetate. Evaporation of the ethyl acetate gives 5-(3-chloropropyl)tetrazole which is used directly in the next step.

Workup

  1. additionThe reaction mixture is poured onto ice
  2. extractionextracted twice with ethyl acetate
  3. extractionextracted with ethylacetate
  4. customEvaporation of the ethyl acetate

Sources & evidence

ORD record
ord-60732cbe8e204ac7b16193d8c91aef6c
Source dataset
uspto-grants-1989_10
Patent number
US04874769

Reaction notes

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