Formic Acid → HCID 14230762, compound

HRID 465257Notes

Reaction equation

HRID 465257 reaction equation
C([NH:20][C:21]1[S:22][CH:23]=[C:24](/[C:26](=[N:31]/[O:32][CH2:33][CH:34]=[CH2:35])/[C:27]([O:29][CH3:30])=[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:31]/[O:32][CH2:33][CH:34]=[CH2:35])/[C:27]([O:29][CH3:30])=[O:28])[N:25]=1

Participants

4

Reactant 2

HCID 284Formic AcidHCID 14230767HCID 14230767, compound

Product 1

HCID 14230762HCID 14230762, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
60 °C

Procedure

In 32 ml of tetrahydrofuran is dissolved 6.45 g of methyl 2-(2-tritylamino-4-thiazolyl)-(Z)-2-allyloxyiminoacetate, followed by addition of 32 ml of 50% formic acid. The mixture is stirred at 60° C. for 40 minutes. The reaction mixture is concentrated under reduced pressure and the solid residue is dissolved in ethyl acetate, washed with aqueous sodium hydrogen carbonate and aqueous sodium chloride in this order, and dried over anhydrous sodium sulfate. The solvent is then distilled off under reduced pressure and the residue is purified by column chromatography [silica gel: 150 g; eluent: hexane-ethyl acetate (1:1)]. The solvent is distilled off and the solid residue is washed with hexane and a small amount of ether in this order, and then dried to give methyl 2-(2-amino-4-thiazolyl)-(Z)-2-allyloxyiminoacetate, m.p. 133°-134° C.

Workup

  1. concentrationThe reaction mixture is concentrated under reduced pressure
  2. dissolutionthe solid residue is dissolved in ethyl acetate
  3. washwashed with aqueous sodium hydrogen carbonate and aqueous sodium chloride in this order
  4. dry with materialdried over anhydrous sodium sulfate
  5. distillationThe solvent is then distilled off under reduced pressure
  6. customthe residue is purified by column chromatography [silica gel: 150 g; eluent: hexane-ethyl acetate (1:1)]
  7. distillationThe solvent is distilled off
  8. washthe solid residue is washed with hexane
  9. dry with materiala small amount of ether in this order, and then dried

Sources & evidence

ORD record
ord-603b303fc16c4db4820a86c1e727d9bc
Source dataset
uspto-grants-1985_10
Patent number
US04550105

Reaction notes

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