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

HRID 887611노트

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HRID 887611 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+].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]

참가 물질

5

반응물 3

HCID 11430Potassium CarbonateHCID 31374DimethylacetamideHCID 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 (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.

후처리

  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

출처 및 근거

ORD 기록
ord-70a204466cf446209170b62194869b28
출처 데이터셋
uspto-grants-2012_08
특허 번호
US08247430B2

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