Formic Acid → HCID 14230762, compound

HRID 2231593Notes

Reaction equation

HRID 2231593 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-a44f2c1d82ae44e2be30871531b291de
Source dataset
uspto-grants-1988_11
Patent number
US04782147

Reaction notes

Loading…