Sodium Bicarbonate → Ethyl 2-(2-aminothiazol-4-yl)-2-methoxyiminoacetate

HRID 1650412Notes

Reaction equation

HRID 1650412 reaction equation
[CH3:1][O:2][N:3]=[C:4]([C:10]([CH2:12]Cl)=O)[C:5]([O:7][CH2:8][CH3:9])=[O:6].[NH2:14][C:15]([NH2:17])=[S:16].C([O-])(=O)C.[Na+].C(=O)(O)[O-].[Na+]>CO.O>[CH3:1][O:2][N:3]=[C:4]([C:10]1[N:14]=[C:15]([NH2:17])[S:16][CH:12]=1)[C:5]([O:7][CH2:8][CH3:9])=[O:6]

Participants

7

Reactant 4

HCID 516892Sodium BicarbonateHCID 517045Sodium AcetateHCID 2723790ThioureaHCID 3017525Ethyl 4-chloro-2-(methoxyimino)-3-oxobutanoate

Product 1

HCID 581091Ethyl 2-(2-aminothiazol-4-yl)-2-methoxyiminoacetateYield 68.5%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

Ethyl 2-methoxyimino-4-chloroacetoacetate (syn isomer) (50 g.) was added over 3 minutes with stirring at ambient temperature to a solution of thiourea (18.4 g.) and sodium acetate (19.8 g.) in a mixture of methanol (250 ml.) and water (250 ml.). After stirring for 35 minutes at 40° to 45° C., the reaction mixture was cooled with ice and adjusted to pH 6.3 with a saturated aqueous solution of sodium bicarbonate. After stirring for 30 minutes at the same temperature, precipitates were collected by filtration, washed with water (200 ml.) and then with diisopropyl ether (100 ml.), and dried to give colorless crystals of ethyl 2-methoxyimino-2-(2-amino-1,3-thiazol-4-yl)acetate (syn isomer) (37.8 g.), m.p. 161° to 162° C.

Workup

  1. temperaturethe reaction mixture was cooled with ice
  2. stirringAfter stirring for 30 minutes at the same temperature
  3. customprecipitates
  4. filtrationwere collected by filtration
  5. washwashed with water (200 ml.)
  6. dry with materialwith diisopropyl ether (100 ml.), and dried

Sources & evidence

ORD record
ord-796df1e19d8a4411854c5fb7c26e0c75
Source dataset
uspto-grants-1990_05
Patent number
US04923998

Reaction notes

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