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

HRID 543941
Notes
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Reaction equation

HRID 543941 reaction equation
C([O-])(=O)C.[Na+].[CH2:6]([O:10][N:11]=[C:12]([C:18](=O)[CH2:19]Cl)[C:13]([O:15][CH2:16][CH3:17])=[O:14])[CH2:7][CH2:8][CH3:9].[NH2:22][C:23]([NH2:25])=[S:24].C(=O)([O-])[O-].[Na+].[Na+]>C(O)C.O>[NH2:25][C:23]1[S:24][CH:19]=[C:18]([C:12](=[N:11][O:10][CH2:6][CH2:7][CH2:8][CH3:9])[C:13]([O:15][CH2:16][CH3:17])=[O:14])[N:22]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 10340Sodium CarbonateHCID 517045Sodium Acetate2×HCID 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 702
Ethanol
Solvent
HCID 962WaterSolvent

Procedure

I.R. νmaxFilm : 1740, 1710, 1470, 1370 cm-1 ( 3) 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-bf247bdcfb5e42a79477e5153b1e706b
Source dataset
uspto-grants-1984_05
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US04447430

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes