2-Methylbenzoic acid → N-methoxy-N,2-dimethylbenzamide

HRID 1506118노트

반응식

HRID 1506118 반응식
[CH3:1][C:2]1[CH:10]=[CH:9][CH:8]=[CH:7][C:3]=1[C:4](O)=[O:5].Cl.CN(C)CCCN=C=NCC.C(N(CC)C(C)C)(C)C.Cl.[CH3:33][NH:34][O:35][CH3:36]>C(Cl)(Cl)Cl.O>[CH3:36][O:35][N:34]([CH3:33])[C:4](=[O:5])[C:3]1[CH:7]=[CH:8][CH:9]=[CH:10][C:2]=1[CH3:1]

참가 물질

7

반응물 4

HCID 83732-Methylbenzoic acidHCID 81138Methanamine, N-methoxy-, hydrochloride (1:1)HCID 81531Diisopropylethylamine2회HCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride

생성물 1

HCID 11344340N-methoxy-N,2-dimethylbenzamide수율 50%

시약·촉매·용매 2

HCID 962Water용매HCID 6212Chloroform용매

실험 절차

2-Methylbenzoic acid (1.00 g, 7.34 mmol) and 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (1.69 g, 8.81 mmol) in chloroform (10 mL) stirred with N,N-diisopropylethylamine (1.50 mL, 8.81 mmol) for 10 minutes under cooling with ice and then stirred with N,O-dimethylhydroxylamine hydrochloride (860 mg, 8.81 mmol) and N,N-diisopropylethylamine (1.50 mL, 8.81 mmol) for one day while the temperature was gradually raised to room temperature. After addition of water, the reaction mixture was extracted with chloroform, and the organic layer was washed with saturated aqueous sodium chloride, dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (hexane/ethyl acetate=1/1 (v/v)) to give the title compound as a pale yellow oil (658 mg, yield 50%).

후처리

  1. temperatureunder cooling with ice
  2. extractionthe reaction mixture was extracted with chloroform
  3. washthe organic layer was washed with saturated aqueous sodium chloride
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by silica gel column chromatography (hexane/ethyl acetate=1/1 (v/v))

출처 및 근거

ORD 기록
ord-f332df48841040e29b262f78ae2862ba
출처 데이터셋
uspto-grants-2015_12
특허 번호
US09216999B2

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