Allyl bromide → N-allyl-N-(2-trifluoromethylphenyl)-2-pyridinesulfonamide 1-oxide

HRID 3750

Reaction equation

HRID 3750 reaction equation
[F:1][C:2]([F:21])([F:20])[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[NH:9][S:10]([C:13]1[N+:14]([O-:19])=[CH:15][CH:16]=[CH:17][CH:18]=1)(=[O:12])=[O:11].[H-].[Na+].[CH2:24](Br)[CH:25]=[CH2:26]>CN(C=O)C>[CH2:26]([N:9]([C:4]1[CH:5]=[CH:6][CH:7]=[CH:8][C:3]=1[C:2]([F:20])([F:1])[F:21])[S:10]([C:13]1[N+:14]([O-:19])=[CH:15][CH:16]=[CH:17][CH:18]=1)(=[O:12])=[O:11])[CH:25]=[CH2:24]

Participants

5

Reactant 3

HCID 7841Allyl bromideHCID 24758Sodium hydrideHCID 20152991N-(2-trifluoromethylphenyl)-2-pyridinesulfonamide 1-oxide

Product 1

HCID 14097714N-allyl-N-(2-trifluoromethylphenyl)-2-pyridinesulfonamide 1-oxide

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To N-(2-trifluoromethylphenyl)-2-pyridinesulfonamide 1-oxide (compound 129, Table A) (1.0 g, 3.0 mmol) in 10 ml of DMF is added NaH (0.30 g, 6.2 mmol) under N2, and the mixture is stirred at RT for 30 minutes. Allyl bromide (0.82 g, 0.59 ml, 6.8 mmol) is added dropwise, and the mixture is stirred at RT for 48 hours. It is then worked up and purified to give the title compound (compound 37, Table A). (DMF is dimethylformamide; RT is room temperature.)

Workup

  1. stirringthe mixture is stirred at RT for 48 hours
  2. custompurified

Sources & evidence

ORD record
ord-032d77276ec347c0b8611cfd56e26b51
Source dataset
uspto-grants-1988_02
Patent number
US04722749

Linked notes

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