Potassium Carbonate → HCID 19081540, compound

HRID 963428Notes

Reaction equation

HRID 963428 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][S:9]([C:12]([F:15])([F:14])[F:13])(=[O:11])=[O:10])=[CH:4][CH:3]=1.[CH3:16][O:17][C:18]1[CH:25]=[CH:24][C:21]([CH2:22]Cl)=[CH:20][CH:19]=1.C(=O)([O-])[O-].[K+].[K+]>CC(C)=O>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([N:8]([CH2:22][C:21]2[CH:24]=[CH:25][C:18]([O:17][CH3:16])=[CH:19][CH:20]=2)[S:9]([C:12]([F:15])([F:13])[F:14])(=[O:11])=[O:10])=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 699934-Methyloxybenzyl chlorideHCID 2133889N-(4-bromophenyl)-1,1,1-trifluoromethanesulfonamide

Product 1

HCID 19081540HCID 19081540, compoundYield 97.1%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A suspension of 1.52 g (5 mmol) of N-(4-bromophenyl)-C,C,C-trifluoro-methanesulphonamide (Example 13bv)), 1.56 g (10 mmol) of 4-methoxybenzyl chloride and 1.38 g (10 mmol) of powdered potassium carbonate in 15 ml of acetone was stirred at reflux for 18 hours. Thereafter, the mixture was concentrated and the residue was taken up in 100 ml of water and 100 ml of ethyl acetate, the organic phase was separated and the aqueous phase was extracted twice with 100 ml of ethyl acetate each time. The combined organic phases were washed neutral with sat. sodium chloride solution, dried over magnesium sulphate and evaporated. The resulting yellow oil was subjected to flash chromatography with hexane/ethyl acetate 95:5. 2.06 g (97%) of N-(4-bromophenyl)-C,C,C-trifluoro-N-(4-methoxy-benzyl)-methanesulphonamide were obtained as a colourless, viscous oil. MS (EI): 423 and 425 (M+, 3%), 121 ([CH2 --C6H4 --OCH3 ]+, 100%).

Workup

  1. temperatureat reflux for 18 hours
  2. concentrationThereafter, the mixture was concentrated
  3. custom100 ml of ethyl acetate, the organic phase was separated
  4. extractionthe aqueous phase was extracted twice with 100 ml of ethyl acetate each time
  5. washThe combined organic phases were washed neutral with sat. sodium chloride solution
  6. dry with materialdried over magnesium sulphate
  7. customevaporated

Sources & evidence

ORD record
ord-51aa466157d748d69ac40372760d75ac
Source dataset
uspto-grants-1998_06
Patent number
US05763450

Reaction notes

Loading…