Benzene, 1-iodo-4-(trifluoromethyl)- → 4-(4-Trifluoromethylphenyl)-thiomorpholin-3-one

HRID 1168684Notes

Reaction equation

HRID 1168684 reaction equation
[NH:1]1[CH2:6][CH2:5][S:4][CH2:3][C:2]1=[O:7].[F:8][C:9]([F:18])([F:17])[C:10]1[CH:15]=[CH:14][C:13](I)=[CH:12][CH:11]=1>[Cu]>[F:8][C:9]([F:18])([F:17])[C:10]1[CH:15]=[CH:14][C:13]([N:1]2[CH2:6][CH2:5][S:4][CH2:3][C:2]2=[O:7])=[CH:12][CH:11]=1

Participants

4

Reactant 2

HCID 67993Benzene, 1-iodo-4-(trifluoromethyl)-HCID 884021,4-Tetrahydrothiazine-3-one

Product 1

HCID 120830104-(4-Trifluoromethylphenyl)-thiomorpholin-3-oneYield 23.3%

Reagents, catalysts & solvents 1

HCID 23978CopperCatalyst

Conditions

Temperature
192.5 °C

Procedure

A mixture of thiomorpholin-3-one (500 mg, 4.27 mmol), 4-trifluoromethyl-1-iodobenzene (1.25 mL, 8.5 mmol) and copper metal (814 mg, 12.8 mmol) was heated in a sealed glass tube at 185-200° C. for 18 hours. The residue was then purified by flash chromatography to give 260 mg of the title product as a white solid.

Workup

  1. customThe residue was then purified by flash chromatography

Sources & evidence

ORD record
ord-5aa1203e24aa48d2a8c27166eb75bfea
Source dataset
uspto-grants-2003_09
Patent number
US06627627B2

Reaction notes

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