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Potassium Carbonate → N-(4-bromophenyl)-C,C,C-trifluoro-N-(4-methoxy-benzyl)-methanesulphonamide

HRID 963428
ノート
印刷プレビュー

反応式

HRID 963428 の反応式
[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
参加物実験手順後処理出典と根拠反応ノート

参加物

5

反応物 3

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

生成物 1

HCID 19081540N-(4-bromophenyl)-C,C,C-trifluoro-N-(4-methoxy-benzyl)-methanesulphonamide収率 97.1%

試薬・触媒・溶媒 1

HCID 180Acetone溶媒

実験手順

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%).

後処理

  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

出典と根拠

ORDレコード
ord-51aa466157d748d69ac40372760d75ac
出典データセット
uspto-grants-1998_06
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US05763450

反応ノート

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