Water → HCID 54007970, compound

HRID 256423Notes

Reaction equation

HRID 256423 reaction equation
[CH3:1][O:2][N:3]=[C:4]([C:10](=O)[CH:11](Cl)[CH3:12])[C:5]([O:7][CH2:8][CH3:9])=[O:6].[NH2:15][C:16]([NH2:18])=[S:17].C([O-])(=O)C.[Na+].O>C(O)C>[NH2:18][C:16]1[S:17][C:11]([CH3:12])=[C:10]([C:4](=[N:3][O:2][CH3:1])[C:5]([O:7][CH2:8][CH3:9])=[O:6])[N:15]=1

Participants

6

Reactant 4

HCID 962WaterHCID 517045Sodium AcetateHCID 2723790ThioureaHCID 53884675HCID 53884675, compound

Product 1

HCID 54007970HCID 54007970, compoundYield 17.7%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
40 °C

Procedure

A mixture of ethyl 2-methoxyimino-2-(2-chloropropionyl)acetate (16.0 g.), thiourea (8.2 g.), sodium acetate (8.9 g.), water (50 ml.) and ethanol (50 ml.) was stirred at 40° C. for 3 hrs. Ethanol was distilled off in vacuo from the reaction mixture. Diisopropyl ether was added to the aqueous solution and stirred. The resultant precipitates were collected by filtration to give ethyl 2-(2-amino-5-methylthiazol-4-yl)-2-methoxyiminoacetate (syn isomer, 3.1 g.). The diisopropyl ether layer was separated from the filtrate, washed with water and an aqueous solution of sodium chloride successively, dried over magnesium sulfate and then filtered. The filtrate was evaporated in vacuo and the oily residue was treated with n-hexane. The precipitates were collected by filtration and washed with a small amount of diisopropyl ether to give the same product (0.9 g.) as above. Total yield 4.0 g.

Workup

  1. distillationEthanol was distilled off in vacuo from the reaction mixture
  2. additionDiisopropyl ether was added to the aqueous solution
  3. stirringstirred
  4. customThe resultant precipitates
  5. filtrationwere collected by filtration

Sources & evidence

ORD record
ord-d4770599284d4f1b903a97e6ae287ec7
Source dataset
uspto-grants-1987_10
Patent number
US04703046

Reaction notes

Loading…