Hydrochloric Acid → HCID 53744847, compound

HRID 1759644Notes

Reaction equation

HRID 1759644 reaction equation
[CH:1]([NH:3][C:4]1[S:5][CH:6]=[C:7]([C:9](=[N:15][O:16][CH2:17][S:18][CH3:19])[C:10]([O:12]CC)=[O:11])[N:8]=1)=[O:2].[OH-].[Na+].Cl>CO>[CH:1]([NH:3][C:4]1[S:5][CH:6]=[C:7]([C:9](=[N:15][O:16][CH2:17][S:18][CH3:19])[C:10]([OH:12])=[O:11])[N:8]=1)=[O:2]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 53862511HCID 53862511, compound

Product 1

HCID 53744847HCID 53744847, compoundYield 51.9%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Conditions

Temperature
30 °C

Procedure

A mixture of ethyl 2-(2-formamidothiazol-4-yl)-2-methylthiomethoxyiminoacetate (syn isomer, 2.4 g.), 1 N aqueous sodium hydroxide (23.8 ml.) and methanol (19.8 ml.) was stirred at 30° C. for 2.5 hours. The resultant solution was adjusted to pH 7 with 10% hydrochloric acid and methanol was distilled off in vacuo. The aqueous solution was adjusted to pH 1 with 10% hydrochloric acid under ice cooling, and extracted with ethyl acetate three times. The extracts were washed with a saturated aqueous solution of sodium chloride, dried over magnesium sulfate and concentrated in vacuo to give 2-(2-formamidothiazol-4-yl)-2-methylthiomethoxyiminoacetic acid (syn isomer, 1.13 g.), mp. 157° C. (dec.).

Workup

  1. distillationwas distilled off in vacuo
  2. extractionextracted with ethyl acetate three times
  3. washThe extracts were washed with a saturated aqueous solution of sodium chloride
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-db46343136ca42e4862ee1d3e54067ed
Source dataset
uspto-grants-1982_07
Patent number
US04341775

Reaction notes

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