4-Chlorobutyronitrile → HCID 178478461, compound

HRID 2074030Notes

Reaction equation

HRID 2074030 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-d06e642e69c4432da6e9dc2c890e86ab
Source dataset
uspto-grants-1990_04
Patent number
US04920132

Reaction notes

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