Diisopropyl Ether → 2-(2-Formamidothiazol-4-yl)-2-(2-formyloxyethoxyimino)acetic acid

HRID 27273Notes

Reaction equation

HRID 27273 reaction equation
[C:1]([O:4][C:5](=O)[CH3:6])(=[O:3])C.[NH2:8][C:9]1[S:10][CH:11]=[C:12]([C:14](=[N:18][O:19]CCO)[C:15]([OH:17])=[O:16])[N:13]=1.[CH:23]([O:26]C(C)C)(C)C>C(O)=O>[CH:23]([NH:8][C:9]1[S:10][CH:11]=[C:12]([C:14](=[N:18][O:19][CH2:6][CH2:5][O:4][CH:1]=[O:3])[C:15]([OH:17])=[O:16])[N:13]=1)=[O:26]

Participants

5

Reactant 3

HCID 7914Diisopropyl EtherHCID 7918Acetic AnhydrideHCID 544034702-(2-Aminothiazol-4-yl)-2-(2-hydroxyethoxyimino)acetic acid

Product 1

HCID 541333172-(2-Formamidothiazol-4-yl)-2-(2-formyloxyethoxyimino)acetic acid

Reagents, catalysts & solvents 1

HCID 284Formic AcidSolvent

Procedure

A solution of formic acid (1.6 g.) and acetic anhydride (3.6 g.) was stirred at 50° C. for an hour. After cooling, 2-(2-aminothiazol-4-yl)-2-(2-hydroxyethoxyimino)acetic acid (syn isomer, 1 g.) was added to the solution and stirred at room temperature for 3 hours. Diisopropyl ether was added to the resultant solution, and the precipitates were filtered out. The filtrate was concentrated in vacuo, and the residue was pulverized with diisopropyl ether. The precipitates were collected by filtration to give 2-(2-formamidothiazol-4-yl)-2-(2-formyloxyethoxyimino)acetic acid (syn isomer, 0.7 g.).

Workup

  1. temperatureAfter cooling
  2. filtrationthe precipitates were filtered out
  3. concentrationThe filtrate was concentrated in vacuo
  4. filtrationThe precipitates were collected by filtration

Sources & evidence

ORD record
ord-e1cd387611074e05a33c963b553c4fba
Source dataset
uspto-grants-1980_09
Patent number
US04220761

Reaction notes

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