Water → 2-Chloro-N-[4-(N,2-dimethoxy-2-oxoethanimidoyl)-1,3-thiazol-2-yl]ethanimidic acid

HRID 2049279Notes

Reaction equation

HRID 2049279 reaction equation
[NH2:1][C:2]1[S:3][CH:4]=[C:5]([C:7](=[N:12][O:13][CH3:14])[C:8]([O:10][CH3:11])=[O:9])[N:6]=1.[Cl:15][CH2:16][C:17](Cl)=[O:18].O>CN(C)C(=O)C>[Cl:15][CH2:16][C:17]([NH:1][C:2]1[S:3][CH:4]=[C:5]([C:7](=[N:12][O:13][CH3:14])[C:8]([O:10][CH3:11])=[O:9])[N:6]=1)=[O:18]

Participants

5

Reactant 3

HCID 962WaterHCID 6577Chloroacetyl chlorideHCID 54074940HCID 54074940, compound

Product 1

HCID 537773192-Chloro-N-[4-(N,2-dimethoxy-2-oxoethanimidoyl)-1,3-thiazol-2-yl]ethanimidic acidYield 85.8%

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Procedure

In 90 ml of N,N-dimethylacetamide is dissolved 21.5 g of methyl 2-(2-aminothiazol-4-yl)-2-methoxyiminoacetate (syn-isomer) and, under ice-cooling, 13.6 g of chloroacetyl chloride is added dropwise. The mixture is stirred under ice-cooling for 30 minutes and, then, at room temperature for 30 minutes, after which 500 ml of water is added. The mixture is extracted twice with ethyl acetate and the combined extract is washed with a 5% aqueous solution of sodium hydrogen carbonate and water in that order and dried. On removal of the solvent, there is obtained 25 g of methyl 2-(2-chloroacetamidothiazol-4-yl)-2-methoxyiminoacetate(syn-isomer) as crystals melting at 130.8° C.

Workup

  1. temperatureunder ice-cooling
  2. temperaturecooling for 30 minutes
  3. extractionThe mixture is extracted twice with ethyl acetate
  4. extractionthe combined extract
  5. washis washed with a 5% aqueous solution of sodium hydrogen carbonate and water in that order
  6. customdried
  7. customOn removal of the solvent

Sources & evidence

ORD record
ord-c22ac43a97aa41a1ac091514da5b5619
Source dataset
uspto-grants-1980_04
Patent number
US04197298

Reaction notes

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