Acetic Anhydride → Ethyl 2-(formylamino)-alpha-oxo-4-thiazoleacetate

HRID 1155154Notes

Reaction equation

HRID 1155154 reaction equation
C(OC(=O)C)(=[O:3])C.[Mn]([O-])(=O)(=O)=O.[K+].[CH:14]([NH:16][C:17]1[S:18][CH:19]=[C:20]([CH2:22][C:23]([O:25][CH2:26][CH3:27])=[O:24])[N:21]=1)=[O:15]>C(O)(=O)C>[CH:14]([NH:16][C:17]1[S:18][CH:19]=[C:20]([C:22](=[O:3])[C:23]([O:25][CH2:26][CH3:27])=[O:24])[N:21]=1)=[O:15]

Participants

6

Reactant 4

HCID 7918Acetic AnhydrideHCID 516875Potassium PermanganateHCID 688091Ethyl 2-formamidothiazol-4-acetateHCID 178470762HCID 178470762, compound

Product 1

HCID 2733245Ethyl 2-(formylamino)-alpha-oxo-4-thiazoleacetate

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A mixture of manganous acetate tetrahydrate (120 g.), acetic acid (1000 ml) and acetic anhydride (100 ml.) was stirred for 20 minutes in an oil bath heated at 130° to 135° C., and to the mixture was added potassium permanganate (20 g.) over 5 minutes at 105° to 110° C. with stirring and then the mixture was further stirred for 30 minutes at 130° to 135° C. The mixture was cooled to room temperature, and to the mixture was added ethyl 2-(2-formylaminothiazol-4-yl)acetate, which can be represented as ethyl 2-(2-formylimino-2,3-dihydrothiazol-4-yl)acetate, (53.5 g.), and then the mixture was stirred for 15 hours at 38° to 40° C. under introduction of air at the rate of 6000 ml. per minute. After the reaction, the precipitates were collected by filtration. The precipitates were washed with acetic acid and water in turn and then dried to give ethyl 2-(2-formylaminothiazol-4-yl)glyoxylate, which can be represented as ethyl 2-(2-formylimino-2,3-dihydrothiazol-4-yl)glyoxylate, (41.5 g.), mp 232° to 233° C. (dec.).

Workup

  1. temperatureheated at 130° to 135° C.
  2. stirringwith stirring
  3. stirringthe mixture was further stirred for 30 minutes at 130° to 135° C
  4. stirringthe mixture was stirred for 15 hours at 38° to 40° C. under introduction of air at the rate of 6000 ml
  5. customAfter the reaction
  6. filtrationthe precipitates were collected by filtration
  7. washThe precipitates were washed with acetic acid and water in turn
  8. customdried

Sources & evidence

ORD record
ord-8d9c0ab8b4c945bdb25d3e4a1f4279b4
Source dataset
uspto-grants-1981_11
Patent number
US04299829

Reaction notes

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