Hydrochloric Acid → HCID 53744847, compound

HRID 1659740Notes

Reaction equation

HRID 1659740 reaction equation
[CH3:1][S:2][CH2:3][O:4][N:5]=[C:6]([C:12]1[N:13]=[C:14]([NH:17][CH:18]=[O:19])[S:15][CH:16]=1)[C:7]([O:9]CC)=[O:8].[OH-].[Na+].Cl>CO>[CH3:1][S:2][CH2:3][O:4][N:5]=[C:6]([C:12]1[N:13]=[C:14]([NH:17][CH:18]=[O:19])[S:15][CH:16]=1)[C:7]([OH:9])=[O:8]

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-methylthiomethoxyimino-2-(2-formamidothiazol-4-yl)acetate (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-methylthiomethoxyimino-2-(2-formamidothiazol-4-yl)acetic 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-13fd973306ba4107bc7ddb3103b750ad
Source dataset
uspto-grants-1981_12
Patent number
US04304770

Reaction notes

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