Sodium Acetate → HCID 73653992, compound

HRID 1195520Notes

Reaction equation

HRID 1195520 reaction equation
[Cl:1][C:2]([Cl:21])([Cl:20])[CH2:3][O:4][C:5]([CH2:7][O:8][N:9]=[C:10]([C:16](=O)[CH2:17]Cl)[C:11]([O:13][CH2:14][CH3:15])=[O:12])=[O:6].[NH2:22][C:23]([NH2:25])=[S:24].C([O-])(=O)C.[Na+]>C(O)C.O>[NH2:25][C:23]1[S:24][CH:17]=[C:16]([C:10](=[N:9][O:8][CH2:7][C:5]([O:4][CH2:3][C:2]([Cl:21])([Cl:20])[Cl:1])=[O:6])[C:11]([O:13][CH2:14][CH3:15])=[O:12])[N:22]=1

Participants

6

Reactant 3

HCID 517045Sodium AcetateHCID 2723790ThioureaHCID 54145401HCID 54145401, compound

Product 1

HCID 73653992HCID 73653992, compoundYield 51.1%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Conditions

Temperature
40 °C

Procedure

A mixture of ethyl 2-(2,2,2-trichloroethoxycarbonylmethoxyimino)-4-chloro-3-oxobutyrate (20 g), thiourea (3.9 g) and sodium acetate (4.2 g) in ethanol (50 ml) and water (50 ml) was stirred at 40° C. for 5 hours. After removal of the solvent from the reaction mixture, the residue was triturated with diisopropyl ether. The precipitates were collected by filtration and washed with diisopropyl ether to give ethyl 2-(2-aminothiazol-4-yl)-2-(2,2,2-trichloroethoxycarbonylmethoxyimino)acetate (syn isomer) (10.6 g), mp 138°-141° C.

Workup

  1. customAfter removal of the solvent from the reaction mixture
  2. customthe residue was triturated with diisopropyl ether
  3. filtrationThe precipitates were collected by filtration
  4. washwashed with diisopropyl ether

Sources & evidence

ORD record
ord-1670d78abcf34f71b18335d8294e616f
Source dataset
uspto-grants-1992_05
Patent number
US05110921

Reaction notes

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