18-Crown-6 → [1-(2-Azidoethyl)-2-(phenylmethylene)hydrazino]oxoacetic acid, ethyl ester

HRID 851781Notes

Reaction equation

HRID 851781 reaction equation
Br[CH2:2][CH2:3][N:4]([C:13](=[O:19])[C:14]([O:16][CH2:17][CH3:18])=[O:15])[N:5]=[CH:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.[N-:20]=[N+:21]=[N-:22].CN(C)C(=[NH2+])N(C)C.C1OCCOCCOCCOCCOCCOC1>CC(C)=O>[N:20]([CH2:2][CH2:3][N:4]([C:13](=[O:19])[C:14]([O:16][CH2:17][CH3:18])=[O:15])[N:5]=[CH:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)=[N+:21]=[N-:22]

Participants

5

Reactant 3

HCID 2855718-Crown-6HCID 86736837[1-(2-Bromoethyl)-2-(phenylmethylene)hydrazino]oxoacetic acid, ethyl esterHCID 178484365HCID 178484365, compound

Product 1

HCID 86736838[1-(2-Azidoethyl)-2-(phenylmethylene)hydrazino]oxoacetic acid, ethyl ester

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

11 g. of the ethyl ester product from part (c) are added to acetone along with 5.7 g. of tetramethylguanidinium azide and 0.05 g. of 18-Crown-6. The mixture is refluxed for eight hours. After distilling off the solvent, the reaction mixture is stirred with 50 ml. of methylene chloride. The organic phase, after drying and concentrating, leaves an oil which crystallizes in the form of white crystals upon the addition of a small amount of isopropanol to yield [1-(2-azidoethyl)-2-(phenylmethylene)hydrazino]oxoacetic acid, ethyl ester; m.p. 59°-61°.

Workup

  1. temperatureThe mixture is refluxed for eight hours
  2. distillationAfter distilling off the solvent
  3. customThe organic phase, after drying
  4. concentrationconcentrating
  5. customleaves an oil which
  6. customcrystallizes in the form of white crystals upon the addition of a small amount of isopropanol

Sources & evidence

ORD record
ord-5daba4e4f6e44f36b7bb2954fb72dae8
Source dataset
uspto-grants-1983_05
Patent number
US04386199

Reaction notes

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