Cyanogen Chloride → 5-Chloro-1H-tetrazole-1-acetic acid ethyl ester

HRID 1659529Notes

Reaction equation

HRID 1659529 reaction equation
[N:1]([CH2:4][C:5]([O:7][CH2:8][CH3:9])=[O:6])=[N+:2]=[N-:3].[N:10]#[C:11][Cl:12]>C(OCC)(=O)C>[Cl:12][C:11]1[N:1]([CH2:4][C:5]([O:7][CH2:8][CH3:9])=[O:6])[N:2]=[N:3][N:10]=1

Participants

4

Reactant 2

HCID 10477Cyanogen ChlorideHCID 69480Acetic acid, azido-, ethyl ester

Product 1

HCID 127857925-Chloro-1H-tetrazole-1-acetic acid ethyl esterYield 78%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 130 g. (1 mole) of ethyl azidoacetate prepared as described in part A and 96 g. (1.56 mole) of cyanogen chloride was heated at a temperature of 125° C. for 20 hours. After the reaction mixture had cooled, the reaction product mixture was dissolved in ethyl acetate, and the solution was filtered and evaporated in vacuo yielding a yellow crystalline mass of product. The yellow crystals were recrystallized from aqueous ethyl alcohol and gave 149 g. (78% yield) of ethyl 5-chloro-1H-tetrazol-1-ylacetate as pale yellow crystals melting at about 57°-60° C.

Workup

  1. additionA mixture of 130 g
  2. temperatureAfter the reaction mixture had cooled
  3. filtrationthe solution was filtered
  4. customevaporated in vacuo
  5. customyielding a yellow crystalline mass of product
  6. customThe yellow crystals were recrystallized from aqueous ethyl alcohol
  7. customgave 149 g

Sources & evidence

ORD record
ord-f5622d0c75284b4f8da3013a80737dda
Source dataset
uspto-grants-1981_12
Patent number
US04304774

Reaction notes

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