Sodium Bicarbonate → HCID 54216521, compound

HRID 1758368Notes

Reaction equation

HRID 1758368 reaction equation
Cl.[NH2:2][C:3]1[S:4][CH:5]=[C:6]([C:8](=[N:14][O:15][CH2:16][CH2:17][O:18][CH2:19][CH3:20])[C:9]([O:11][CH2:12][CH3:13])=[O:10])[N:7]=1.C(=O)(O)[O-].[Na+]>O.C(OCC)(=O)C>[NH2:2][C:3]1[S:4][CH:5]=[C:6]([C:8](=[N:14][O:15][CH2:16][CH2:17][O:18][CH2:19][CH3:20])[C:9]([O:11][CH2:12][CH3:13])=[O:10])[N:7]=1

Participants

5

Reactant 2

HCID 516892Sodium BicarbonateHCID 73664961HCID 73664961, compound

Product 1

HCID 54216521HCID 54216521, compoundYield 86.7%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

A suspension of ethyl 2-(2-aminothiazol-4-yl)-2-(2-ethoxyethoxyimino)acetate hydrochloride (syn isomer, 16.9 g.) in a mixture of water (170 ml.) and ethyl acetate (200 ml.) was adjusted to pH 6.5 with sodium bicarbonate and the ethyl acetate layer was separated. The aqueous layer was extracted with ethyl acetate (100 ml.), and the exacts were combined together, washed with a saturated aqueous solution of sodium chloride, dried and then concentrated in vacuo. The oily residue was triturated with n-hexane. The precipitates were collected by filtration and washed with n-hexane to give ethyl 2-(2-aminothiazol-4-yl)-2-(2-ethoxyethoxyimino)acetate (syn isomer, 13 g.).

Workup

  1. customthe ethyl acetate layer was separated
  2. extractionThe aqueous layer was extracted with ethyl acetate (100 ml.)
  3. washwashed with a saturated aqueous solution of sodium chloride
  4. customdried
  5. concentrationconcentrated in vacuo
  6. customThe oily residue was triturated with n-hexane
  7. filtrationThe precipitates were collected by filtration
  8. washwashed with n-hexane

Sources & evidence

ORD record
ord-1b34069f516b45858c5ad29f23076ee5
Source dataset
uspto-grants-1983_02
Patent number
US04372952

Reaction notes

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