Hydrochloric Acid → HCID 54222530, compound

HRID 745367Notes

Reaction equation

HRID 745367 reaction equation
[CH:1]([NH:3][C:4]1[S:5][CH:6]=[C:7]([C:9](=[N:15][O:16][CH2:17][CH2:18][O:19][CH2:20][CH3:21])[C:10]([O:12]CC)=[O:11])[N:8]=1)=[O:2].Cl>[OH-].[Na+]>[CH2:20]([O:19][CH2:18][CH2:17][O:16][N:15]=[C:9]([C:7]1[N:8]=[C:4]([NH:3][CH:1]=[O:2])[S:5][CH:6]=1)[C:10]([OH:12])=[O:11])[CH3:21]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 54079007HCID 54079007, compound

Product 1

HCID 54222530HCID 54222530, compoundYield 80.7%

Reagents, catalysts & solvents 1

HCID 14798Sodium HydroxideSolvent

Procedure

A solution of ethyl 2-(2-formamidothiazol-4-yl)-2-(2-ethoxyethoxyimino)acetate (syn isomer, 4.35 g.) in 1N aqueous sodium hydroxide (33 ml.) was stirred below 10° C. for 3 hours. The resultant solution was adjusted to pH 7.0 with conc. hydrochloric acid under ice cooling and washed with ethyl acetate. To the aqueous solution was added ethyl acetate and adjusted to pH 1.5 with hydrochloric acid under ice cooling. The ethyl acetate layer was separated and the aqueous layer was extracted with ethyl acetate. The extracts were combined together, washed with a saturated aqueous solution of sodium chloride, dried and then concentrated in vacuo. The oily residue was dissolved in diethyl ether and n-hexane was added to the solution until the solution became clear. The solution was stirred for an hour, and the precipitates were collected by filtration and washed with n-hexane to give 2-(2-ethoxyethoxyimino)-2-(2-formamidothiazol-4-yl)acetic acid (syn isomer, 3.2 g.).

Workup

  1. washwashed with ethyl acetate
  2. additionTo the aqueous solution was added ethyl acetate
  3. customThe ethyl acetate layer was separated
  4. extractionthe aqueous layer was extracted with ethyl acetate
  5. washwashed with a saturated aqueous solution of sodium chloride
  6. customdried
  7. concentrationconcentrated in vacuo
  8. dissolutionThe oily residue was dissolved in diethyl ether
  9. additionn-hexane was added to the solution until the solution
  10. filtrationthe precipitates were collected by filtration
  11. washwashed with n-hexane

Sources & evidence

ORD record
ord-10e907c970674bf98ce512dbe813264f
Source dataset
uspto-grants-1986_07
Patent number
US04598147

Reaction notes

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