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

HRID 1154105Notes

Reaction equation

HRID 1154105 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>[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

4

Reactant 2

HCID 284Formic AcidHCID 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 8028TetrahydrofuranSolvent

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 concentrating the 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. concentrationAfter concentrating the resultant solution in vacuo
  2. dissolutionthe residue was dissolved in ethyl acetate
  3. washwashed with an aqueous solution of sodium bicarbonate
  4. dry with materiala saturated aqueous solution of sodium chloride in turn, and dried over magnesium sulfate
  5. concentrationAfter concentrating the resultant solution in vacuo

Sources & evidence

ORD record
ord-db13cffa15084bef8227faab92e271bd
Source dataset
uspto-grants-1984_12
Patent number
US04487767

Reaction notes

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