Aniline → 3-Bromo-N-phenyl-1-(phenylsulfonyl)-1H-pyrrole-2-carboxamide

HRID 524992

反応式

HRID 524992 の反応式
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C[Al](C)C.[Br:12][C:13]1[CH:17]=[CH:16][N:15]([S:18]([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)(=[O:20])=[O:19])[C:14]=1[C:27](OC)=[O:28].O.O.C(C(C(C([O-])=O)O)O)([O-])=O.[Na+].[Na+]>C1(C)C=CC=CC=1.O>[Br:12][C:13]1[CH:17]=[CH:16][N:15]([S:18]([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)(=[O:20])=[O:19])[C:14]=1[C:27]([NH:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)=[O:28]

参加物

7

反応物 4

HCID 6115AnilineHCID 517351Sodium tartrate-2-hydrateHCID 16682925Trimethylaluminum2 回HCID 44518095Methyl 3-bromo-1-(phenylsulfonyl)-1H-pyrrole-2-carboxylate

生成物 1

HCID 709789713-Bromo-N-phenyl-1-(phenylsulfonyl)-1H-pyrrole-2-carboxamide収率 114.7%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 1140Toluene溶媒2 回

実験手順

In a three-necked round-bottom flask aniline (1.57 mL, 17.20 mmol) was dissolved in 80 mL of toluene under inert atmosphere. To this solution was added trimethy aluminium (7.82 mL, 15.64 mmol) and the mixture was stirred at room temperature during 10 minutes. Afterwards, a solution methyl 3-bromo-1-(phenylsulfonyl)-1H-pyrrole-2-carboxylate (2.0 g, 5.81 mmol) in 20 mL of toluene were added and the reaction mixtures was heated at 80° C. for 3 h. Next, the mixture was allowed to cool to room temperature and 20-30 mL of water was added to hydrolyze unreacted trimethyl aluminium and a 0,5M aqueous solution of disodium tartrate dihydrate was also added. After stirring for a while, the two layers were separated and the aqueous phase was extracted with ethyl acetate. The organic mixture was washed with the same 0,5M aqueous solution of disodium tartrate dehydrate (200 mL), water and brine, dried and concentrated in vacuum to afford 2.7 g of a residue that was used in the following step without further purification.

後処理

  1. customthe reaction mixtures
  2. temperaturewas heated at 80° C. for 3 h
  3. temperatureto cool to room temperature
  4. stirringAfter stirring for a while
  5. customthe two layers were separated
  6. extractionthe aqueous phase was extracted with ethyl acetate
  7. washThe organic mixture was washed with the same 0,5M aqueous solution of disodium tartrate dehydrate (200 mL), water and brine
  8. customdried
  9. concentrationconcentrated in vacuum

出典と根拠

ORDレコード
ord-434824392d9f4be38e6a4fad389651c9
出典データセット
uspto-grants-2016_05
特許番号
US09340547B2

関連ノート

読み込み中…