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

HRID 491625노트

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HRID 491625 반응식
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]

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

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온도
0 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-338acbf132884d52a85c9a8c8ad80720
출처 데이터셋
uspto-grants-2009_05
특허 번호
US07531553B2

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