Sodium Acetate → 2-(2-Aminothiazole-4-yl)-2-methoxyiminoacetic acid

HRID 1164261Notes

Reaction equation

HRID 1164261 reaction equation
[NH2:1][C:2]([NH2:4])=[S:3].C([O-])(=O)C.[Na+].[CH3:10][O:11][N:12]=[C:13]([C:17](=O)[CH:18](Br)Br)[C:14]([OH:16])=[O:15]>O1CCCC1.O>[NH2:1][C:2]1[S:3][CH:18]=[C:17]([C:13](=[N:12][O:11][CH3:10])[C:14]([OH:16])=[O:15])[N:4]=1

Participants

6

Reactant 3

HCID 517045Sodium AcetateHCID 2723790ThioureaHCID 542636792-Methoxyimino-3-oxo-4,4-dibromobutyric acid

Product 1

HCID 1252162-(2-Aminothiazole-4-yl)-2-methoxyiminoacetic acidYield 40.6%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
30 °C

Procedure

Thiourea (377 mg) and sodium acetate (406 mg) were added to a solution of 2-methoxyimino-3-oxo-4,4-dibromobutyric acid (syn isomer, 500 mg) in tetrahydrofuran (5 ml) and water (5 ml), and the solution was stirred at 30° C. for 4 hours. The solution was adjusted to pH 3.5, concentrated under reduced pressure and allowed to stand at 0° C. overnight. The precipitates were collected by filtration, washed with water and dried to give 2-(2-aminothiazol-4-yl)-2-methoxyiminoacetic acid (syn isomer, 135 mg).

Workup

  1. concentrationconcentrated under reduced pressure
  2. waitto stand at 0° C. overnight
  3. filtrationThe precipitates were collected by filtration
  4. washwashed with water
  5. customdried

Sources & evidence

ORD record
ord-e90dac36570648d7a4bcc2e85bd63361
Source dataset
uspto-grants-1983_01
Patent number
US04368325

Reaction notes

Loading…