Tetrahydrofuran → 2-(2-Aminothiazol-4-yl)-2-allyloxyiminoacetic acid

HRID 1905190Notes

Reaction equation

HRID 1905190 reaction equation
[NH2:1][C:2]1[S:3][CH:4]=[C:5]([C:7](=[N:13][O:14][CH2:15][CH:16]=[CH2:17])[C:8]([O:10]CC)=[O:9])[N:6]=1.[OH-].[Na+].O1CCCC1>CO>[NH2:1][C:2]1[S:3][CH:4]=[C:5]([C:7](=[N:13][O:14][CH2:15][CH:16]=[CH2:17])[C:8]([OH:10])=[O:9])[N:6]=1

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 14798Sodium HydroxideHCID 54209614Ethyl 2-(2-aminothiazol-4-yl)-2-allyloxyiminoacetate

Product 1

HCID 544842532-(2-Aminothiazol-4-yl)-2-allyloxyiminoacetic acidYield 59.6%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of ethyl 2-(2-aminothiazol-4-yl)-2-allyloxyiminoacetate (syn isomer, 3.6 g.), 2N aqueous solution of sodium hydroxide (14.1 ml.), tetrahydrofuran (14.1 ml.) and methanol (15 ml.) was stirred at 40° C. for 1.5 hours. The resultant solution was concentrated in vacuo, and the residue was dissolved in water. After the solution was adjusted to pH 2.8 with 10% hydrochloric acid under ice cooling, the precipitates were collected by filtration, washed with water and acetone in turn and dried to give 2-(2-aminothiazol-4-yl)-2-allyloxyiminoacetic acid (syn isomer, 1.91 g.), mp 187° C. (dec.).

Workup

  1. concentrationThe resultant solution was concentrated in vacuo
  2. dissolutionthe residue was dissolved in water
  3. filtrationthe precipitates were collected by filtration
  4. washwashed with water and acetone in turn
  5. customdried

Sources & evidence

ORD record
ord-70f53b3adc4e458cbd408c0e4a5f8e91
Source dataset
uspto-grants-1989_06
Patent number
US04841062

Reaction notes

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