Tetrabutylammonium Fluoride → N-(4-Bromo-2-iodophenyl)benzenesulfonamide

HRID 400588

反応式

HRID 400588 の反応式
[F-].C([N+](CCCC)(CCCC)CCCC)CCC.[C:19]1([S:25]([N:28](S(C2C=CC=CC=2)(=O)=O)[C:29]2[CH:34]=[CH:33][C:32]([Br:35])=[CH:31][C:30]=2[I:36])(=[O:27])=[O:26])[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1>C1COCC1.C(OCC)(=O)C.Cl>[Br:35][C:32]1[CH:33]=[CH:34][C:29]([NH:28][S:25]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)(=[O:27])=[O:26])=[C:30]([I:36])[CH:31]=1

参加物

6

反応物 2

HCID 2724141Tetrabutylammonium FluorideHCID 60026850N,N-bisbenzenesulfonyl-(4-bromo-2-iodoaniline)

生成物 1

HCID 60026307N-(4-Bromo-2-iodophenyl)benzenesulfonamide収率 90.2%

試薬・触媒・溶媒 3

HCID 313Hydrochloric Acid溶媒HCID 8028Tetrahydrofuran溶媒HCID 8857Ethyl Acetate溶媒

実験手順

A solution of tetrabutylammonium fluoride (1 M in THF, 11 mL) in 30 mL of THF was treated with N,N-bisbenzenesulfonyl-(4-bromo-2-iodoaniline) (5.78 g, 10 mmol) in several portions. After 18 hours, the mixture was diluted with of 40 mL of ethyl acetate and 40 mL of 1 N HCl. The phases were separated and the aqueous layer was extracted with two 40 mL portions of ethyl acetate. The combined organic layers were washed with two 20 mL portions of 1 N HCl, two 20 mL portions of saturated aqueous sodium bicarbonate solution, 20 mL of brine, dried over magnesium sulfate, filtered, and concentrated in vacuo to afford 3.95 g (90% yield) of the title compound as a solid, which was used without further purification.

後処理

  1. customThe phases were separated
  2. extractionthe aqueous layer was extracted with two 40 mL portions of ethyl acetate
  3. washThe combined organic layers were washed with two 20 mL portions of 1 N HCl, two 20 mL portions of saturated aqueous sodium bicarbonate solution, 20 mL of brine
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

出典と根拠

ORDレコード
ord-f48f7c3ff64b4f578e03f54458b9a514
出典データセット
uspto-grants-2014_06
特許番号
US08741897B2

関連ノート

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