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

HRID 1577735Notes

Reaction equation

HRID 1577735 reaction equation
[C:1](OC(=O)C)(=[O:3])C.[CH2:8]([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])[CH2:9][CH3:10]>C(O)=O>[CH2:8]([O:11][N:12]=[C:13]([C:17]1[N:18]=[C:19]([NH:22][CH:1]=[O:3])[S:20][CH:21]=1)[C:14]([OH:16])=[O:15])[CH2:9][CH3:10]

Participants

4

Reactant 2

HCID 7918Acetic AnhydrideHCID 540960402-(2-Amino-4-thiazolyl)-2-propoxyiminoacetic acid

Product 1

HCID 536876672-(2-Formamidothiazol-4-yl)-2-propoxyiminoacetic acidYield 78.5%

Reagents, catalysts & solvents 1

HCID 284Formic AcidSolvent

Procedure

Formic acid (17.5 g.) was added dropwise to acetic anhydride (38.8 g.) over 3 to 4 minutes with stirring and ice-cooling, and the mixture was stirred for 1 hour at 50° C. 2-n-Propoxyimino-2-(2-amino-1,3-thiazol-4-yl)acetic acid (syn isomer) (21.8 g.) was added thereto with stirring and ice-cooling, and the mixture was stirred for 2.5 hours at ambient temperature. The reaction mixture was concentrated to dryness under reduced pressure, and the residue was pulverized with diisopropyl ether. The powder was collected by filtration and dried to give 2-n-propoxyimino-2-(2-formamido-1,3-thiazol-4-yl)acetic acid (syn isomer) (19.2 g.).

Workup

  1. temperatureice-cooling
  2. stirringthe mixture was stirred for 1 hour at 50° C
  3. stirringwith stirring
  4. temperatureice-cooling
  5. stirringthe mixture was stirred for 2.5 hours at ambient temperature
  6. concentrationThe reaction mixture was concentrated to dryness under reduced pressure
  7. filtrationThe powder was collected by filtration
  8. customdried

Sources & evidence

ORD record
ord-d9566f21854849dab4f1e4e2224a7ba7
Source dataset
uspto-grants-1981_09
Patent number
US04288436

Reaction notes

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