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

HRID 434880Notes

Reaction equation

HRID 434880 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-3aa5459688b04a2f8e7c763a8f635020
Source dataset
uspto-grants-1983_08
Patent number
US04399133

Reaction notes

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