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

HRID 2412770Notes

Reaction equation

HRID 2412770 reaction equation
[C:1]([O:4][C:5](=O)[CH3:6])(=[O:3])C.OCC[O:11][N:12]=[C:13]([C:17]1[N:18]=[C:19]([NH2:22])[S:20][CH:21]=1)[C:14]([OH:16])=[O:15].[CH:23]([O:26]C(C)C)(C)C>C(O)=O>[CH:1]([O:4][CH2:5][CH2:6][O:11][N:12]=[C:13]([C:17]1[N:18]=[C:19]([NH:22][CH:23]=[O:26])[S:20][CH:21]=1)[C:14]([OH:16])=[O:15])=[O:3]

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-hydroxyethoxyimino)-2-(2-amino thiazol-4-yl)acetic acid (syn isomer) (1 g.) was added to the solution and stirred at ambient temperature for 3 hours. Diisopropyl ether was added to the resultant solution, and the precipitates were filtered off. The filtrate was concentrated in vacuo, and the residue was pulverized with diisopropyl ether. The precipitates were collected by filtration to give 2-(2-formyloxyethoxyimino)-2-(2-formamidothiazol-4-yl)acetic acid (syn isomer) (0.7 g.).

Workup

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

Sources & evidence

ORD record
ord-20f5498d660d4bc499741189e57b8c09
Source dataset
uspto-grants-1985_01
Patent number
US04493833

Reaction notes

Loading…