Tributylstannane → 2-Ethoxycarbonylimino-3-(3-trifluoromethylphenyl)thiazoline

HRID 22037

Reaction equation

HRID 22037 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)[CH:10]=[C:9](Br)[S:8]1)=[O:5])[CH3:2].C([SnH](CCCC)CCCC)CCC.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1>O1CCCC1>[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]=[CH:9][S:8]1)=[O:5])[CH3:2]

Participants

5

Reactant 3

HCID 5948TributylstannaneHCID 7187Benzoyl PeroxideHCID 540969932-Ethoxycarbonylimino-3-(3-trifluoromethylpheny)-5-bromothiazoline

Product 1

HCID 543520892-Ethoxycarbonylimino-3-(3-trifluoromethylphenyl)thiazolineYield 75.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 2-ethoxycarbonylimino-3-(3-trifluoromethylphenyl)-5-bromothiazoline (4.7 g), tributyltin hydride (6.9 g) and a catalytic amount of benzoyl peroxide in tetrahydrofuran (100 ml) was refluxed for 10 hours. The solvent was removed by distillation, and the residue was washed with hexane. Recrystallization from a mixture of hexane and ethanol gave 2.85 g of 2-ethoxycarbonylimino-3-(3-trifluoromethylphenyl) thiazoline (Compound (xii)).

Workup

  1. customThe solvent was removed by distillation
  2. washthe residue was washed with hexane
  3. customRecrystallization
  4. additionfrom a mixture of hexane and ethanol

Sources & evidence

ORD record
ord-c6888d67ee3542789f12cd043e1c654d
Source dataset
uspto-grants-1995_06
Patent number
US05426188

Linked notes

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