Dimethyl Sulfide → N,N-Diethyl-4-methoxy-2-(methylthio)benzamide

HRID 2267459노트

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HRID 2267459 반응식
N[C@H](C(O)=O)C[SeH].[Li]CCCC.CN(C)CCN(C)C.[CH2:21]([N:23]([CH2:34][CH3:35])[C:24](=[O:33])[C:25]1[CH:30]=[CH:29][C:28]([O:31][CH3:32])=[CH:27][CH:26]=1)[CH3:22].[CH3:36][S:37]C>C1COCC1>[CH2:34]([N:23]([CH2:21][CH3:22])[C:24](=[O:33])[C:25]1[CH:30]=[CH:29][C:28]([O:31][CH3:32])=[CH:27][C:26]=1[S:37][CH3:36])[CH3:35]

참가 물질

6

반응물 4

HCID 1068Dimethyl SulfideHCID 8037N,N,N',N'-TetramethylethylenediamineHCID 231459N,N-Diethyl-para-anisamideHCID 178511841HCID 178511841, 화합물

생성물 1

HCID 57428875N,N-Diethyl-4-methoxy-2-(methylthio)benzamide

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

실험 절차

Sec-BuLi (1.4 M in cyclohexane, 11.34 mL, 15 mmol) was carefully added to a mixture of N,N,N′,N′-tetramethylethane-1,2-diamine (2.2 mL, 15 mmol) in anhydrous THF at −78° C. N,N-Diethyl-4-methoxybenzamide (3 g, 14.4 mmol) dissolved in 5 mL of anhydrous THF was added dropwise to the reaction mixture which was allowed to stir for 1 h. Dimethyl sulfide (2.5 mL, 28.8 mmol) was then added to the reaction. After stirring for 15 min, the cooling bath was removed and the mixture was stirred overnight. The reaction was diluted with ethyl acetate and washed with a solution of saturated sodium bicarbonate, water and then brine. The organic layer was then dried with sodium sulfate, concentrated and purified by flash chromatography using a gradient of 20 to 80% ethyl acetate in hexanes to obtain the product as a light yellow oil. Yield=2.51 g. MS (M+H)+ 254.

후처리

  1. additionwas added dropwise to the reaction mixture which
  2. stirringAfter stirring for 15 min
  3. customthe cooling bath was removed
  4. stirringthe mixture was stirred overnight
  5. additionThe reaction was diluted with ethyl acetate
  6. washwashed with a solution of saturated sodium bicarbonate, water
  7. dry with materialThe organic layer was then dried with sodium sulfate
  8. concentrationconcentrated
  9. custompurified by flash chromatography

출처 및 근거

ORD 기록
ord-30dadc65744642a58f7f34e3f021c1fa
출처 데이터셋
uspto-grants-2010_12
특허 번호
US07858785B2

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