Sodium Bicarbonate → HCID 54074940, compound

HRID 2049278Notes

Reaction equation

HRID 2049278 reaction equation
Br[CH2:2][C:3](=O)[C:4](=[N:9][O:10][CH3:11])[C:5]([O:7][CH3:8])=[O:6].O.O.O.C([O-])(=O)C.[Na+].[NH2:21][C:22]([NH2:24])=[S:23].C(=O)([O-])O.[Na+]>O1CCCC1.O>[NH2:24][C:22]1[S:23][CH:2]=[C:3]([C:4](=[N:9][O:10][CH3:11])[C:5]([O:7][CH3:8])=[O:6])[N:21]=1

Participants

7

Reactant 4

HCID 516892Sodium BicarbonateHCID 2723790ThioureaHCID 23665404Sodium Acetate TrihydrateHCID 53841316HCID 53841316, compound

Product 1

HCID 54074940HCID 54074940, compoundYield 52.7%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

In 350 ml of tetrahydrofuran is dissolved 52 g of methyl 4-bromo-3-oxo-2-methoxyiminobutyrate, followed by addition of 250 ml of water. Then, 89.1 g of sodium acetate trihydrate and 33.2 g of thiourea are added and the mixture is reacted with stirring at room temperature for 18 hours. To this reaction mixture is added 200 ml of a 5% aqueous solution of sodium hydrogen carbonate and the mixture is extracted with ethyl acetate. The organic layer is washed with water, dried and distilled under reduced pressure to remove the solvent. To the residue is added 200 ml of ether and the resultant crystals are collected by filtration. By the above procedure is obtained 24.8 g of methyl 2-(2-aminothiazol-4-yl)-2-methoxyiminoacetate (syn-isomer) as crystals melting at 164.9° C.

Workup

  1. customthe mixture is reacted
  2. extractionthe mixture is extracted with ethyl acetate
  3. washThe organic layer is washed with water
  4. customdried
  5. distillationdistilled under reduced pressure
  6. customto remove the solvent
  7. additionTo the residue is added 200 ml of ether
  8. filtrationthe resultant crystals are collected by filtration

Sources & evidence

ORD record
ord-c911d4351b3140698eb92cd93ad515b3
Source dataset
uspto-grants-1980_04
Patent number
US04197298

Reaction notes

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