Sodium Carbonate → Ethyl 2-(2-aminothiazol-4-yl)-2-n-butoxyiminoacetate

HRID 1650430Notes

Reaction equation

HRID 1650430 reaction equation
[CH2:1]([O:5][N:6]=[C:7]([C:13](=O)[CH2:14]Cl)[C:8]([O:10][CH2:11][CH3:12])=[O:9])[CH2:2][CH2:3][CH3:4].[NH2:17][C:18]([NH2:20])=[S:19].C([O-])(=O)C.[Na+].C(=O)([O-])[O-].[Na+].[Na+]>C(O)C.O>[NH2:20][C:18]1[S:19][CH:14]=[C:13]([C:7](=[N:6][O:5][CH2:1][CH2:2][CH2:3][CH3:4])[C:8]([O:10][CH2:11][CH3:12])=[O:9])[N:17]=1

Participants

7

Reactant 4

HCID 10340Sodium CarbonateHCID 517045Sodium AcetateHCID 2723790ThioureaHCID 54055311Ethyl 2-(butoxyimino)-4-chloro-3-oxobutanoate

Product 1

HCID 54097425Ethyl 2-(2-aminothiazol-4-yl)-2-n-butoxyiminoacetateYield 63.8%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

A solution of ethyl 2-n-butoxyimino-4-chloro-3-oxobutyrate (syn isomer, 52.1 g.), thiourea (15.9 g.), sodium acetate 3 hydrate (28.4 g.), water (130 ml.) and ethanol (180 ml.) was stirred at 40° C. for 1.25 hours. The resultant solution was adjusted to pH 6.5 with an aqueous solution of sodium carbonate under ice cooling, and stirred for 20 minutes under ice cooling. The precipitates were collected by filtration, and washed with water and diisopropyl ether in turn to give ethyl 2-(2-aminothiazol-4-yl)-2-n-butoxyiminoacetate (syn isomer, 36.1 g.), mp 126° to 128° C.

Workup

  1. filtrationThe precipitates were collected by filtration
  2. washwashed with water and diisopropyl ether in turn

Sources & evidence

ORD record
ord-fa30590e09ff411cb9606582e9eece80
Source dataset
uspto-grants-1990_05
Patent number
US04923998

Reaction notes

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