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

HRID 2211645노트

반응식

HRID 2211645 반응식
[C:1]([C:5]1[CH:10]=[CH:9][C:8]([N+:11]([O-])=[O:12])=[CH:7][C:6]=1[NH:14][C:15](=[O:20])[CH2:16][N:17]([CH3:19])[CH3:18])([CH3:4])([CH3:3])[CH3:2]>CCO.O1CCOCC1>[NH4+:11].[OH-:12].[NH2:11][C:8]1[CH:9]=[CH:10][C:5]([C:1]([CH3:4])([CH3:3])[CH3:2])=[C:6]([NH:14][C:15](=[O:20])[CH2:16][N:17]([CH3:18])[CH3:19])[CH:7]=1

참가 물질

5

반응물 1

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

생성물 2

HCID 14923Ammonium HydroxideHCID 21961467HCID 21961467, 화합물

시약·촉매·용매 2

HCID 702Ethanol용매HCID 312751,4-Dioxane용매

실험 절차

N-(2-tert-Butyl-5-nitro-phenyl)-2-dimethylamino-acetamide (25.8 g, 92 mmol) was dissolved in EtOH (1.4 L) and 1,4-dioxane (200 mL). The solution was degassed under vacuum with stirring. 10% Pd/C (2.5 g) was added (as a slurry in EtOH). The mixture was degassed again, then the reaction vessel was charged with H2 gas (balloon) and stirred overnight at RT. The reaction was filtered through Celite® with MeOH and the filtrate was concentrated under reduced pressure. The recovered material was eluted through a 36×7 cm column of silica gel with a 97.5:2.5:0.25 and 95:5:0.5 CH2Cl2:MeOH:NH4OH(aq) step gradient giving N-(5-amino-2-tert-butyl-phenyl)-2-dimethylamino-acetamide as a brown solid.

후처리

  1. customThe solution was degassed under vacuum
  2. addition10% Pd/C (2.5 g) was added (as a slurry in EtOH)
  3. customThe mixture was degassed again
  4. additionthe reaction vessel was charged with H2 gas (balloon)
  5. stirringstirred overnight at RT
  6. filtrationThe reaction was filtered through Celite® with MeOH
  7. concentrationthe filtrate was concentrated under reduced pressure
  8. washThe recovered material was eluted through a 36×7 cm column of silica gel with a 97.5:2.5:0.25 and 95:5:0.5 CH2Cl2

출처 및 근거

ORD 기록
ord-fc22478adad04de9b8cd23c38215d7ba
출처 데이터셋
uspto-grants-2006_09
특허 번호
US07101868B2

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