Ethanol → HCID 73664961, compound

HRID 255740Notes

Reaction equation

HRID 255740 reaction equation
[Cl:1][CH2:2][C:3](=O)[C:4](=[N:10][O:11][CH2:12][CH2:13][O:14][CH2:15][CH3:16])[C:5]([O:7][CH2:8][CH3:9])=[O:6].[NH2:18][C:19]([NH2:21])=[S:20].C([O-])(=O)C.[Na+].C(O)C>O>[ClH:1].[NH2:21][C:19]1[S:20][CH:2]=[C:3]([C:4](=[N:10][O:11][CH2:12][CH2:13][O:14][CH2:15][CH3:16])[C:5]([O:7][CH2:8][CH3:9])=[O:6])[N:18]=1

Participants

6

Reactant 4

HCID 702EthanolHCID 517045Sodium AcetateHCID 2723790ThioureaHCID 54289985HCID 54289985, compound

Product 1

HCID 73664961HCID 73664961, compoundYield 33.4%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
40 °C

Procedure

A mixture of ethyl 4-chloro-2-(2-ethoxyethoxyimino)-3-oxobutyrate (syn isomer, 56.5 g.), thiourea (19.4 g.), sodium acetate (20.9 g.), ethanol (140 ml.) and water (140 ml.) was stirred at 40° C. for 5 hours. After removing the ethanol from the resultant solution in vacuo, the aqueous solution was adjusted to pH 6.5 with aqueous sodium bicarbonate and then extracted with ethyl acetate. Conc. hydrochloric acid was added to the stirred ethyl acetate extract under ice-cooling to form the precipitates. The precipitates were collected by filtration washed with chilled water and diethyl ether in turn and dried over phosphorus pentoxide under reduced pressure to give ethyl 2-(2-aminothiazol-4-yl)-2-(2-ethoxyethoxyimino)acetate hydrochloride (syn isomer, 23 g.).

Workup

  1. customAfter removing the ethanol from the resultant solution in vacuo
  2. extractionextracted with ethyl acetate
  3. additionConc. hydrochloric acid was added to the stirred ethyl acetate
  4. extractionextract under ice-
  5. temperaturecooling
  6. customto form the precipitates
  7. filtrationThe precipitates were collected by filtration
  8. washwashed with chilled water and diethyl ether in turn
  9. dry with materialdried over phosphorus pentoxide under reduced pressure

Sources & evidence

ORD record
ord-568b23d21b0d479897b4614073c146d3
Source dataset
uspto-grants-1987_10
Patent number
US04698337

Reaction notes

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