Dimethylamine → N-(2-tert-butyl-5-nitrophenyl)-2-(dimethylamino)acetamide

HRID 491625ノート

反応式

HRID 491625 の反応式
Br[CH2:2][C:3]([NH:5][C:6]1[CH:11]=[C:10]([N+:12]([O-:14])=[O:13])[CH:9]=[CH:8][C:7]=1[C:15]([CH3:18])([CH3:17])[CH3:16])=[O:4].C([O-])([O-])=O.[K+].[K+].[CH3:25][NH:26][CH3:27]>C1COCC1>[C:15]([C:7]1[CH:8]=[CH:9][C:10]([N+:12]([O-:14])=[O:13])=[CH:11][C:6]=1[NH:5][C:3](=[O:4])[CH2:2][N:26]([CH3:27])[CH3:25])([CH3:18])([CH3:17])[CH3:16]

参加物

5

反応物 3

HCID 674DimethylamineHCID 11430Potassium CarbonateHCID 219613852-bromo-N-(2-tert-butyl-5-nitrophenyl)acetamide

生成物 1

HCID 21961377N-(2-tert-butyl-5-nitrophenyl)-2-(dimethylamino)acetamide

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

反応条件

温度
0 °C

実験手順

2-Bromo-N-(2-tert-butyl-5-nitro-phenyl)-acetamide (Step B, 80 g, 253 mmol) and K2CO3 (70 g, 506 mmol) were combined in a 3 L 3-neck round bottom flask fitted with a mechanical stirrer, N2(g) inlet, and pressure equalizing addition funnel. THF (1.75 L) was added and the mixture cooled to 0° C. under N2(g). N,N-Dimethylamine (400 mL of a 2 M solution in THF, 800 mmol) was added to the mixture through the pressure equalizing addition funnel over 30 min. The mixture was gradually warmed to RT with stirring overnight. The reaction was quenched by filtering under vacuum and concentrating the filtrate under reduced pressure. The recovered material was eluted through a 36×7 cm column of silica gel with 50% EtOAc:Hexanes giving a brown solid.

後処理

  1. customfitted with a mechanical stirrer, N2(g) inlet
  2. additionaddition funnel
  3. additionaddition funnel over 30 min
  4. temperatureThe mixture was gradually warmed to RT
  5. customThe reaction was quenched
  6. filtrationby filtering under vacuum
  7. concentrationconcentrating the filtrate under reduced pressure
  8. washThe recovered material was eluted through a 36×7 cm column of silica gel with 50% EtOAc

出典と根拠

ORDレコード
ord-338acbf132884d52a85c9a8c8ad80720
出典データセット
uspto-grants-2009_05
特許番号
US07531553B2

反応ノート

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