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

HRID 22029

Reaction equation

HRID 22029 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-trifluoromethylpheny)-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-e9219addc6ce432f8c50f7527d001711
Source dataset
uspto-grants-1995_06
Patent number
US05426188

Linked notes

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