O-Toluidine → 1-(Phenylsulfonyl)-N-o-tolyl-3-(trifluoromethyl)-1H-pyrrole-2-carboxamide

HRID 524981

反応式

HRID 524981 の反応式
[NH2:1][C:2]1[C:3]([CH3:8])=[CH:4][CH:5]=[CH:6][CH:7]=1.C[Al](C)C.[C:13]1([S:19]([N:22]2[CH:26]=[CH:25][C:24]([C:27]([F:30])([F:29])[F:28])=[C:23]2[C:31](OC)=[O:32])(=[O:21])=[O:20])[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.O.O.C(C(C(C([O-])=O)O)O)([O-])=O.[Na+].[Na+]>C1(C)C=CC=CC=1.O>[C:13]1([S:19]([N:22]2[CH:26]=[CH:25][C:24]([C:27]([F:30])([F:28])[F:29])=[C:23]2[C:31]([NH:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=2[CH3:8])=[O:32])(=[O:20])=[O:21])[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=1

参加物

7

反応物 4

HCID 7242O-ToluidineHCID 517351Sodium tartrate-2-hydrateHCID 16682925Trimethylaluminum2 回HCID 70922372methyl 1-(phenylsulfonyl)-3-(trifluoromethyl)-1H-pyrrole-2-carboxylate

生成物 1

HCID 709223191-(Phenylsulfonyl)-N-o-tolyl-3-(trifluoromethyl)-1H-pyrrole-2-carboxamide収率 221.2%

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 o-toluidine (0.53 g, 5 mmol) was dissolved in 15 mL of toluene under inert atmosphere. To this solution was added trimethy aluminium (2.5 mL, 5 mmol) and the mixture was stirred at room temperature during 10 minutes. Afterwards, a solution of methyl 1-(phenylsulfonyl)-3-(trifluoromethyl)-1H-pyrrole-2-carboxylate (207 mg, 0.62 mmol) in 15 mL of toluene were added and the reaction mixtures was heated at 80° C. over night. Next, the mixture was allowed to cool to room temperature and 2-3 mL of water were added to hydrolyze unreacted trimethyl aluminium and a 0,5M aqueous solution of disodium tartrate dihydrate were added stirring for a while. Afterwards, 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 dihydrate (25 mL), water and brine, dried and concentrated in vacuum to afford 560 mg 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. over night
  3. temperatureto cool to room temperature
  4. stirringstirring for a while
  5. customAfterwards, the 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 dihydrate (25 mL), water and brine
  8. customdried
  9. concentrationconcentrated in vacuum

出典と根拠

ORDレコード
ord-b338121e6cbf435aa0d26dccff587f2e
出典データセット
uspto-grants-2016_05
特許番号
US09340547B2

関連ノート

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