Methanol → 2-(2-Aminothiazol-4yl)-2-n-butoxyiminoacetic acid

HRID 621230Notes

Reaction equation

HRID 621230 reaction equation
[NH2:1][C:2]1[S:3][CH:4]=[C:5]([C:7](=[N:13][O:14][CH2:15][CH2:16][CH2:17][CH3:18])[C:8]([O:10]CC)=[O:9])[N:6]=1.CO.[OH-].[Na+]>O1CCCC1>[NH2:1][C:2]1[S:3][CH:4]=[C:5]([C:7](=[N:13][O:14][CH2:15][CH2:16][CH2:17][CH3:18])[C:8]([OH:10])=[O:9])[N:6]=1

Participants

5

Reactant 3

HCID 887MethanolHCID 14798Sodium HydroxideHCID 54097425Ethyl 2-(2-aminothiazol-4-yl)-2-n-butoxyiminoacetate

Product 1

HCID 540243022-(2-Aminothiazol-4yl)-2-n-butoxyiminoacetic acidYield 78.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of ethyl 2-(2-aminothiazol-4-yl)-2-n-butoxyiminoacetate (syn isomer, 36 g.), methanol (133 ml.), tetrahydrofuran (133 ml.) and 2N aqueous solution of sodium hydroxide (133 ml.) was stirred at 30° C. for 5 hours. After the resultant solution was concentrated in vacuo, the residue was dissolved in water. The solution was adjusted to pH 7 with 10% hydrochloric acid and treated with activated charcoal. The solution was adjusted to pH 2.0 with 10% hydrochloric acid and stirred for 20 minutes under ice cooling. The precipitates were collected by filtration, washed with water and acetone in turn, and dried to give 2-(2-aminothiazol-4-yl)-2-n-butoxyiminoacetic acid (syn isomer, 25.4 g.).

Workup

  1. concentrationAfter the resultant solution was concentrated in vacuo
  2. dissolutionthe residue was dissolved in water
  3. additiontreated with activated charcoal
  4. filtrationThe precipitates were collected by filtration
  5. washwashed with water and acetone in turn
  6. customdried

Sources & evidence

ORD record
ord-4e80c9d50f25421a8b54c573e3106d4f
Source dataset
uspto-grants-1989_04
Patent number
US04822888

Reaction notes

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