Sodium Methoxide → HCID 54512939, compound

HRID 5324Notes

Reaction equation

HRID 5324 reaction equation
[CH2:1]([N:5]([C:14]1[CH:19]=[CH:18][CH:17]=[C:16]([C:20]([F:23])([F:22])[F:21])[CH:15]=1)[C:6]([NH:8]C(OCC)=O)=[S:7])[CH:2]=[CH:3][CH3:4].C[O-].[Na+]>CO>[CH2:1]([N:5]([C:14]1[CH:19]=[CH:18][CH:17]=[C:16]([C:20]([F:23])([F:21])[F:22])[CH:15]=1)[C:6]([NH2:8])=[S:7])[CH:2]=[CH:3][CH3:4]

Participants

4

Reactant 2

HCID 10942334Sodium MethoxideHCID 54532360HCID 54532360, compound

Product 1

HCID 54512939HCID 54512939, compoundYield 50.5%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of N-crotyl-N-(3-trifluoromethylphenyl)-N'-ethoxycarbonylthiourea (6 g) and sodium methoxide (28 % methanolic solution; 6.6 g) in methanol (100 ml) was refluxed for 2 days. After removal of the solvent, the residue was extracted with chloroform, 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 N-crotyl-N-(3-trifluoromethylphenyl)thiourea (2.4 g). The thus obtained thiourea (2.0 g) and N-bromosuccinimide (1.4 g) were dissolved in chloroform (50 ml), and the resultant solution was stirred at room temperature for 5 hours, washed with an aqueous sodium sulfite solution and dried over anhydrous magnesium sulfate. After removal of the solvent by distillation under reduced pressure, the residue was subjected to column chromatography to give 0.8 g of 2-imino-3-(3-trifluoromethylphenyl)-5-(1-bromoethyl)thiazolidine.

Workup

  1. customAfter removal of the solvent
  2. extractionthe residue was extracted with chloroform
  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-03cf8a9450bf45e38bbedbaf7ee743f1
Source dataset
uspto-grants-1993_09
Patent number
US05244863

Reaction notes

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