Water → HCID 54560759, compound

HRID 745358Notes

Reaction equation

HRID 745358 reaction equation
[Br:1][CH2:2][CH2:3][O:4][N:5]=[C:6]([C:12](=O)[CH2:13]Cl)[C:7]([O:9][CH2:10][CH3:11])=[O:8].[NH2:16][C:17]([NH2:19])=[S:18].O.O.O.C([O-])(=O)C.[Na+].O>C(O)C>[NH2:19][C:17]1[S:18][CH:13]=[C:12]([C:6](=[N:5][O:4][CH2:3][CH2:2][Br:1])[C:7]([O:9][CH2:10][CH3:11])=[O:8])[N:16]=1

Participants

6

Reactant 4

HCID 962WaterHCID 2723790ThioureaHCID 23665404Sodium Acetate TrihydrateHCID 54488460HCID 54488460, compound

Product 1

HCID 54560759HCID 54560759, compoundYield 27.8%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
40 °C

Procedure

A mixture of ethyl 2-(2-bromoethoxyimino)-4-chloro-3-oxobutyrate (syn isomer, 156 g.), thiourea (39.4 g.) sodium acetate trihydrate (70.5 g.), water (300 ml.) and ethanol (500 ml.) was stirred at 40° C. for an hour. The resultant solution was concentrated in vacuo and the resiude was extracted twice with ethyl acetate. The extracts were washed with a saturated aqueous solution of sodium chloride, dried over magnesium sulfate and concentrated in vacuo. After adding diethyl ether (1 l.) to the oily residue, the soluble substance was separated by decantation and the solution was concentrated in vacuo. The residue was crystallized with diisopropyl ether and the precipitates were collected by filtration to give ethyl 2-(2-aminothiazol-4-yl)-2-(2-bromoethoxyimino)acetate (syn isomer, 46.4 g.), mp. 111° to 114° C.

Workup

  1. concentrationThe resultant solution was concentrated in vacuo
  2. extractionthe resiude was extracted twice with ethyl acetate
  3. washThe extracts were washed with a saturated aqueous solution of sodium chloride
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated in vacuo
  6. additionAfter adding diethyl ether (1 l.) to the oily residue
  7. customthe soluble substance was separated by decantation
  8. concentrationthe solution was concentrated in vacuo
  9. customThe residue was crystallized with diisopropyl ether
  10. filtrationthe precipitates were collected by filtration

Sources & evidence

ORD record
ord-eaaff36464774028bf97db5725ae2227
Source dataset
uspto-grants-1986_07
Patent number
US04598147

Reaction notes

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