Formic Acid → Ethyl 2-(2-aminothiazol-4-yl)-2-allyloxyiminoacetate

HRID 1284707Notes

Reaction equation

HRID 1284707 reaction equation
C([NH:20][C:21]1[S:22][CH:23]=[C:24]([C:26](=[N:32][O:33][CH2:34][CH:35]=[CH2:36])[C:27]([O:29][CH2:30][CH3:31])=[O:28])[N:25]=1)(C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.C(O)=O.O1CCCC1>C(OCC)(=O)C>[NH2:20][C:21]1[S:22][CH:23]=[C:24]([C:26](=[N:32][O:33][CH2:34][CH:35]=[CH2:36])[C:27]([O:29][CH2:30][CH3:31])=[O:28])[N:25]=1

Participants

5

Reactant 3

HCID 284Formic AcidHCID 8028TetrahydrofuranHCID 54525939Ethyl 2-(2-tritylaminothiazol-4-yl)-2-allyloxyiminoacetate

Product 1

HCID 54209614Ethyl 2-(2-aminothiazol-4-yl)-2-allyloxyiminoacetateYield 82.9%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

A solution of ethyl 2-(2-tritylaminothiazol-4-yl)-2-allyloxyiminoacetate (syn isomer, 8.7 g.), 50% formic acid (42.5 ml.) and tetrahydrofuran (42.5 ml.) was stirred at 60° C. for 40 minutes. After concentthe resultant solution in vacuo, the residue was dissolved in ethyl acetate, washed with an aqueous solution of sodium bicarbonate and a saturated aqueous solution of sodium chloride in turn, and dried over magnesium sulfate. After concentrating the resultant solution in vacuo, the residue was subjected to column chromatography on silica gel with benzene and ethyl acetate in turn, to give ethyl 2-(2-aminothiazol-4-yl)-2-allyloxyiminoacetate (syn isomer, 3.7 g.), mp. 102° to 104° C.

Workup

  1. washwashed with an aqueous solution of sodium bicarbonate
  2. dry with materiala saturated aqueous solution of sodium chloride in turn, and dried over magnesium sulfate
  3. concentrationAfter concentrating the resultant solution in vacuo

Sources & evidence

ORD record
ord-834c128c0aec433a946e84e7a85fd837
Source dataset
uspto-grants-1986_01
Patent number
US04563522

Reaction notes

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