Triethylamine → N-methoxy-N,3-dimethyl-4-nitrobenzamide

HRID 1507309

반응식

HRID 1507309 반응식
C(N(CC)CC)C.[CH3:8][C:9]1[CH:10]=[C:11]([CH:15]=[CH:16][C:17]=1[N+:18]([O-:20])=[O:19])[C:12](O)=[O:13].Cl.[CH3:22][NH:23][O:24][CH3:25].CCN=C=NCCCN(C)C>C(Cl)Cl>[CH3:25][O:24][N:23]([CH3:22])[C:12](=[O:13])[C:11]1[CH:15]=[CH:16][C:17]([N+:18]([O-:20])=[O:19])=[C:9]([CH3:8])[CH:10]=1

참가 물질

6

반응물 4

HCID 8471TriethylamineHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 183703-Methyl-4-nitrobenzoic acidHCID 81138Methanamine, N-methoxy-, hydrochloride (1:1)

생성물 1

HCID 46318653N-methoxy-N,3-dimethyl-4-nitrobenzamide

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

Triethylamine (7.6 mL, 54.65 mmol) was added slowly to a mixture of 3-methyl-4-nitrobenzoic acid (5 g, 27.33 mmol), N,O-dimethylhydroxylamine hydrochloride (2.99 g, 30.06 mmol), and EDCI (6.28 g, 32.79 mmol) in DCM (30 mL). The mixture was stirred at room temperature overnight, quenched with saturated aqueous NaHCO3 and stirred at room temperature for 30 minutes. Water (50 mL) was added followed by additional DCM. The mixture was stirred for 10 minutes and layers were separated. The aqueous layer was again extracted with DCM. The combined organic layer was dried over Na2SO4, then filtered. The solvent was removed and the residual oil chromatographed (DCM/EtOAc) to provide the title compound as a white solid.

후처리

  1. customquenched with saturated aqueous NaHCO3
  2. stirringstirred at room temperature for 30 minutes
  3. additionWater (50 mL) was added
  4. stirringThe mixture was stirred for 10 minutes
  5. customlayers were separated
  6. extractionThe aqueous layer was again extracted with DCM
  7. dry with materialThe combined organic layer was dried over Na2SO4
  8. filtrationfiltered
  9. customThe solvent was removed
  10. customthe residual oil chromatographed (DCM/EtOAc)

출처 및 근거

ORD 기록
ord-1fda36faeee44a28a7557e93cef30f90
출처 데이터셋
uspto-grants-2015_12
특허 번호
US09221804B2

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