Methanol → HCID 54085586, compound

HRID 745361Notes

Reaction equation

HRID 745361 reaction equation
[CH2:1]([S:4][CH2:5][CH2:6][O:7][N:8]=[C:9]([C:15]1[N:16]=[C:17]([NH:20][CH:21]=[O:22])[S:18][CH:19]=1)[C:10]([O:12]CC)=[O:11])[CH:2]=[CH2:3].CO.[OH-].[Na+]>O1CCCC1>[CH2:1]([S:4][CH2:5][CH2:6][O:7][N:8]=[C:9]([C:15]1[N:16]=[C:17]([NH:20][CH:21]=[O:22])[S:18][CH:19]=1)[C:10]([OH:12])=[O:11])[CH:2]=[CH2:3]

Participants

5

Reactant 3

HCID 887MethanolHCID 14798Sodium HydroxideHCID 54521452HCID 54521452, compound

Product 1

HCID 54085586HCID 54085586, compoundYield 43.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
35 °C

Procedure

A mixture of ethyl 2-(2-allylthioethoxyimino)-2-(2-formamidothiazol-4-yl)acetate (syn isomer, 5.1 g.), methanol (37.2 ml.), 1N-aqueous sodium hydroxide (37.2 ml.) and tetrahydrofuran (35 ml.) was stirred at 35° C. for 5.5 hours. After concentrating the resultant solution in vacuo, the residue was washed with ethyl acetate twice. The aqueous solution was adjusted to pH 1 with 10% hydrochloric acid and extracted with ethyl acetate twice. The extract was washed with a saturated aqueous solution of sodium chloride dried over magnesium sulfate and concentrated in vacuo. The residue was triturated with n-hexane and the precipitates were collected by filtration to give 2-(2-allylthioethoxyimino)-2-(2-formamidothiazol-4-yl)acetic acid (syn isomer, 2.03 g.), mp. 70° to 78° C.

Workup

  1. concentrationAfter concentrating the resultant solution in vacuo
  2. washthe residue was washed with ethyl acetate twice
  3. extractionextracted with ethyl acetate twice
  4. washThe extract was washed with a saturated aqueous solution of sodium chloride
  5. dry with materialdried over magnesium sulfate
  6. concentrationconcentrated in vacuo
  7. customThe residue was triturated with n-hexane
  8. filtrationthe precipitates were collected by filtration

Sources & evidence

ORD record
ord-f9953bef9d4341ea82f2737153351edd
Source dataset
uspto-grants-1986_07
Patent number
US04598147

Reaction notes

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