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

HRID 926461

반응식

HRID 926461 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 (37.9 mL, 273 mmol) was added slowly to a mixture of 3-methyl-4-nitrobenzoic acid (25.0 g, 136 mmol), N,O-dimethylhydroxylamine hydrochloride (14.95 g, 150.3 mmol), and EDCI (31.40 g, 163.9 mmol) in DCM (171 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 layers were dried over MgSO4, then filtered. The solvent was removed and the residual oil chromatographed (0 to 20% EtOAc/DCM) to provide the title compound as a yellow oil.

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 layers were dried over MgSO4
  8. filtrationfiltered
  9. customThe solvent was removed
  10. customthe residual oil chromatographed (0 to 20% EtOAc/DCM)

출처 및 근거

ORD 기록
ord-756dc36076ee4ea598f058289d0fbdd5
출처 데이터셋
uspto-grants-2016_03
특허 번호
US09284308B2

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