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

HRID 888120ノート

反応式

HRID 888120 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+].C[C:26]([N:28](C)[CH3:29])=O>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:28]([CH3:29])[CH3:26])([CH3:18])([CH3:17])[CH3:16]

参加物

5

反応物 3

HCID 11430Potassium CarbonateHCID 31374DimethylacetamideHCID 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 (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 inlet, and pressure equalizing addition funnel. THF (1.75 L) was added and the mixture was cooled to 0° C. under N2. DMA (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 it under vacuum and then 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 N-(2-tert-butyl-5-nitro-phenyl)-2-dimethylamino-acetamide as a brown solid.

後処理

  1. customfitted with a mechanical stirrer, N2 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 it 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-abb1059a1ce445de99feb6d202b8e020
出典データセット
uspto-grants-2012_08
特許番号
US08247556B2

反応ノート

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