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

HRID 1659765Notes

Reaction equation

HRID 1659765 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-7a58d548d9a84ded9a85a2442bc5105a
Source dataset
uspto-grants-1981_12
Patent number
US04304770

Reaction notes

Loading…