N-bromobutanimide → 2-Ethoxycarbonylimino-3-(3-trifluoromethylpheny)-5-bromothiazoline

HRID 1721042Notes

Reaction equation

HRID 1721042 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][CH2:9][S:8]1)=[O:5])[CH3:2].[Br:22]N1C(=O)CCC1=O>C(Cl)(Cl)Cl>[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]([Br:22])[S:8]1)=[O:5])[CH3:2]

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 542258332-Ethoxycarbonylimino-3-(3-trifluoromethylphenyl)thiazolidine

Product 1

HCID 540969932-Ethoxycarbonylimino-3-(3-trifluoromethylpheny)-5-bromothiazolineYield 45.3%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

A solution of 2-ethoxycarbonylimino-3-(3-trifluoromethylphenyl) thiazolidine (1.6 g) and N-bromosuccinimide (2 g) in chloroform (50 ml) was refluxed for 10 hours. After cooling, the reaction mixture was washed with an aqueous sodium sulfite solution and dried over anhydrous magnesium sulfate. The solvent was removed under reduced pressure, and the residue was subjected to column chromatography to give 0.9 g of 2-ethoxycarbonylimino-3-(3-trifluoromethylphenyl)-5-bromothiazoline (Compound No. 30).

Workup

  1. temperatureAfter cooling
  2. washthe reaction mixture was washed with an aqueous sodium sulfite solution
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customThe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-29f33485db5844ac8296bc2d529b5278
Source dataset
uspto-grants-1996_04
Patent number
US05508415

Reaction notes

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