Triethylamine → 3-(N,N-Diethylaminosulfonyl)-N-methoxy-N-methylbenzamide

HRID 2300766

반응식

HRID 2300766 반응식
[CH2:1]([N:3]([CH2:16][CH3:17])[S:4]([C:7]1[CH:8]=[C:9]([CH:13]=[CH:14][CH:15]=1)[C:10](O)=[O:11])(=[O:6])=[O:5])[CH3:2].Cl.[CH3:19][NH:20][O:21][CH3:22].C(N(CC)CC)C.Cl.CN(C)CCCN=C=NCC.C([O-])(O)=O.[Na+]>C(Cl)Cl.CN(C1C=CN=CC=1)C>[CH2:1]([N:3]([CH2:16][CH3:17])[S:4]([C:7]1[CH:8]=[C:9]([CH:13]=[CH:14][CH:15]=1)[C:10]([N:20]([O:21][CH3:22])[CH3:19])=[O:11])(=[O:6])=[O:5])[CH3:2]

참가 물질

8

반응물 5

HCID 8471TriethylamineHCID 81138Methanamine, N-methoxy-, hydrochloride (1:1)HCID 516892Sodium BicarbonateHCID 7945953-(Diethylsulfamoyl)benzoic acidHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride

생성물 1

HCID 183755293-(N,N-Diethylaminosulfonyl)-N-methoxy-N-methylbenzamide수율 38.2%

시약·촉매·용매 2

HCID 142844-(Dimethylamino)pyridine촉매HCID 6344Dichloromethane용매

실험 절차

3-(N,N-diethylaminosulfonyl)benzoic acid (1.17 g, 4.55 mmol) and N,O-dimethylhydroxylamine hydrochloride (498 mg, 5.11 mmol) were dissolved in CH2Cl2 (30 mL). To this solution was added triethylamine (1.9 mL, 14 mmol), 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (970 mg, 5.06 mmol) and 4-(N,N-dimethylamino)pyridine (117 mg, 0.958 mmol). The resulting solution was stirred at room temperature for 17 h then poured into saturated aqueous NaHCO3 and extracted 3× with ethyl acetate. The combined organics were washed with brine then dried over MgSO4 and concentrated under reduced pressure. The residue was purified by column chromatography (silica, 70:30 hexanes:acetone) to yield 522 mg of the title compound.

후처리

  1. extractionextracted 3× with ethyl acetate
  2. washThe combined organics were washed with brine
  3. dry with materialthen dried over MgSO4
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by column chromatography (silica, 70:30 hexanes:acetone)

출처 및 근거

ORD 기록
ord-d58cab61ebb845fb8c8419a52f6cd322
출처 데이터셋
uspto-grants-2002_12
특허 번호
US06498165B1

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