Acetic Anhydride → 2-(2-Formamidothiazol-4-yl)-2-butoxyiminoacetic acid

HRID 848260Notes

Reaction equation

HRID 848260 reaction equation
[C:1](OC(=O)C)(=[O:3])C.[NH2:8][C:9]1[S:10][CH:11]=[C:12]([C:14](=[N:18][O:19][CH2:20][CH2:21][CH2:22][CH3:23])[C:15]([OH:17])=[O:16])[N:13]=1>C(O)=O>[CH:1]([NH:8][C:9]1[S:10][CH:11]=[C:12]([C:14](=[N:18][O:19][CH2:20][CH2:21][CH2:22][CH3:23])[C:15]([OH:17])=[O:16])[N:13]=1)=[O:3]

Participants

4

Reactant 2

HCID 7918Acetic AnhydrideHCID 540243022-(2-Aminothiazol-4yl)-2-n-butoxyiminoacetic acid

Product 1

HCID 541324842-(2-Formamidothiazol-4-yl)-2-butoxyiminoacetic acidYield 72.1%

Reagents, catalysts & solvents 1

HCID 284Formic AcidSolvent

Procedure

Formic acid (18.95 g.) was added dropwise to acetic anhydride (42.0 g.) under stirring at room temperature over 5 minutes, and stirred at 50° C. for an hour. 2-(2-Aminothiazol-4-yl)-2-n-butoxyiminoacetic acid (syn isomer, 25 g.) was added to the solution under ice cooling, and stirred at room temperature for 3 hours and additionally at 30° C. for an hour. After concentrating the resultant solution in vacuo, the residue was dissolved in diethyl ether. The solution was washed with water and a saturated aqueous solution of sodium chloride in turn, dried over magnesium sulfate and concentrated in vacuo. The obtained oil was triturated with a solution of n-hexane (1 part) and diisopropyl ether (1 part), and collected by filtration to give 2-(2-formamidothiazol-4-yl)-2-n-butoxyiminoacetic acid (syn isomer, 20.1 g.).

Workup

  1. stirringstirred at 50° C. for an hour
  2. stirringstirred at room temperature for 3 hours and additionally at 30° C. for an hour
  3. concentrationAfter concentrating the resultant solution in vacuo
  4. dissolutionthe residue was dissolved in diethyl ether
  5. washThe solution was washed with water
  6. dry with materiala saturated aqueous solution of sodium chloride in turn, dried over magnesium sulfate
  7. concentrationconcentrated in vacuo
  8. customThe obtained oil was triturated with a solution of n-hexane (1 part) and diisopropyl ether (1 part)
  9. filtrationcollected by filtration

Sources & evidence

ORD record
ord-28c5e016ddd94480b201e8ef63ced5d6
Source dataset
uspto-grants-1981_10
Patent number
US04294960

Reaction notes

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