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Sodium Bicarbonate → Ethyl 2-(2-amino-4-thiazolyl)-2-ethoxyiminoacetate

HRID 543929
Notes
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Reaction equation

HRID 543929 reaction equation
[CH2:1]([O:3][N:4]=[C:5]([C:11](=O)[CH2:12]Cl)[C:6]([O:8][CH2:9][CH3:10])=[O:7])[CH3:2].[NH2:15][C:16]([NH2:18])=[S:17].C([O-])(=O)C.[Na+].C(=O)(O)[O-].[Na+]>O.CO>[NH2:18][C:16]1[S:17][CH:12]=[C:11]([C:5](=[N:4][O:3][CH2:1][CH3:2])[C:6]([O:8][CH2:9][CH3:10])=[O:7])[N:15]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 516892Sodium BicarbonateHCID 517045Sodium AcetateHCID 2723790ThioureaHCID 53877278Ethyl 4-chloro-2-(ethoxyimino)-3-oxobutanoate

Product 1

HCID 53897917Ethyl 2-(2-amino-4-thiazolyl)-2-ethoxyiminoacetateYield 34.8%

Reagents, catalysts & solvents 2

HCID 887
Methanol
Solvent
HCID 962WaterSolvent

Conditions

Temperature
48 °C

Procedure

A mixture of ethyl 2-ethoxyimino-3-oxo-4-chlorobutyrate (syn isomer 38.7 g.), thiourea (13.2 g.), sodium acetate (14.3 g.), methanol (95 ml.) and water (95 ml.) was stirred at 48° C. for 40 minutes. After the resultant solution was adjusted to pH 6.5 with an aqueous solution of sodium bicarbonate, the appeared precipitates were collected by filtration and washed with diisopropyl ether to give ethyl 2-(2-amino-4-thiazolyl)-2-ethoxyiminoacetate (syn isomer, 14.7 g.), mp 130° to 131° C.

Workup

  1. customthe appeared precipitates
  2. filtrationwere collected by filtration
  3. washwashed with diisopropyl ether

Sources & evidence

ORD record
ord-c75f8b3e1f6245ef83c12c8a4f9fade9
Source dataset
uspto-grants-1984_05
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US04447430

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes