Ethyl cyanoformate → HCID 178470518, compound

HRID 325737Notes

Reaction equation

HRID 325737 reaction equation
C([Sn]([N:14]=[N+:15]=[N-:16])(CCCC)CCCC)CCC.[C:17]([C:19]([O:21][CH2:22][CH3:23])=[O:20])#[N:18]>C1C=CC=CC=1>[NH:18]1[C:17]([C:19]([O:21][CH2:22][CH3:23])=[O:20])=[N:14][N:15]=[N:16]1

Participants

4

Reactant 2

HCID 69336Ethyl cyanoformateHCID 4984872Tributyltin azide

Product 1

HCID 178470518HCID 178470518, compound

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

A solution of tributyltin azide (6.65 g) and ethyl cyanoformate (1.98 g) in dry benzene (25 ml) was heated at reflux for 48 hours. The benzene was removed under reduced pressure and the residue was dissolved in an excess quantity of a dry solution of hydrogen chloride in ethanol. The mixture was allowed to stand, and then the ethanol was removed in vacuo on the rotary evaporator to give a red oil. Chromatography of this oil on a column of silica gel, eluting with a mixture of methanol and chloroform (1:9 v/v), gave ethyl tetrazole-5-carboxylate, identical with samples prepared by the other methods as described above.

Workup

  1. temperatureat reflux for 48 hours
  2. customThe benzene was removed under reduced pressure
  3. dissolutionthe residue was dissolved in an excess quantity of a dry solution of hydrogen chloride in ethanol
  4. customthe ethanol was removed in vacuo on the rotary evaporator
  5. customto give a red oil
  6. washChromatography of this oil on a column of silica gel, eluting with a mixture of methanol and chloroform (1:9 v/v)

Sources & evidence

ORD record
ord-8af80520addd40129ee2c82162302e90
Source dataset
uspto-grants-1984_04
Patent number
US04442115

Reaction notes

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