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

HRID 1074703Notes

Reaction equation

HRID 1074703 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 2 N 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-9511b77cd3aa4831be76959280329cc9
Source dataset
uspto-grants-1983_07
Patent number
US04393059

Reaction notes

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