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Sodium Methoxide → 2-Ethoxycarbonylimino-3-(3-trifluoromethylphenyl) 5-methylthiazoline

HRID 5310
Notes
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Reaction equation

HRID 5310 reaction equation
[CH2:1]([O:3][C:4]([N:6]=[C:7]1[N:11]([C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([C:18]([F:21])([F:20])[F:19])[CH:13]=2)[CH2:10][C:9](=[CH2:22])[S:8]1)=[O:5])[CH3:2].C[O-].[Na+]>C(O)C>[CH2:1]([O:3][C:4]([N:6]=[C:7]1[N:11]([C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([C:18]([F:20])([F:21])[F:19])[CH:13]=2)[CH:10]=[C:9]([CH3:22])[S:8]1)=[O:5])[CH3:2]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

4

Reactant 2

HCID 10942334Sodium MethoxideHCID 540384642-Ethoxycarbonylimino-3-(3-trifluoromethylphenyl)-5-methylenethiazolidine

Product 1

HCID 538034182-Ethoxycarbonylimino-3-(3-trifluoromethylphenyl) 5-methylthiazolineYield 80%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 2-ethoxycarbonylimino-3-(3-tri-fluoromethylphenyl)-5-methylenethiazolidine (2.0 g) and sodium methoxide (28 % methanolic solution; 1.2 g) in ethanol (50 ml) was refluxed for 30 minutes. After removal of the solvent under reduced pressure, the concentrated residue was extracted with chlorofom (200 ml), washed with water and dried over anhydrous magnesium sulfate. The solvent was removed under reduced pressure, and the residue was subjected to column chromatography to give 1.6 g of 2-ethoxycarbonylimino-3-(3-trifluoromethylphenyl)-5-methyl-thiazoline (Compound No. 1).

Workup

  1. customAfter removal of the solvent under reduced pressure
  2. extractionthe concentrated residue was extracted with chlorofom (200 ml)
  3. washwashed with water
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customThe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-b3ec2847d438470ca46e18bcfaff73b8
Source dataset
uspto-grants-1993_09
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05244863

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes