Triethylamine → 2-[(2-Chloro-5-isopropenyl-phenyl)-(3,4-dimethoxy-benzenesulfonyl)-amino]-N,N-diethyl-acetamide

HRID 1674664노트

반응식

HRID 1674664 반응식
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](O)([CH3:10])[CH3:9])=[CH:4][C:3]=1[N:12]([S:21]([C:24]1[CH:29]=[CH:28][C:27]([O:30][CH3:31])=[C:26]([O:32][CH3:33])[CH:25]=1)(=[O:23])=[O:22])[CH2:13][C:14]([N:16]([CH2:19][CH3:20])[CH2:17][CH3:18])=[O:15].CCN(CC)CC.CS(Cl)(=O)=O>C(Cl)Cl.CN(C1C=CN=CC=1)C>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([CH3:10])=[CH2:9])=[CH:4][C:3]=1[N:12]([S:21]([C:24]1[CH:29]=[CH:28][C:27]([O:30][CH3:31])=[C:26]([O:32][CH3:33])[CH:25]=1)(=[O:22])=[O:23])[CH2:13][C:14]([N:16]([CH2:17][CH3:18])[CH2:19][CH3:20])=[O:15]

참가 물질

6

반응물 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 575113202-[[2-chloro-5-(1-hydroxy-1-methyl-ethyl)-phenyl]-(3,4-dimethoxy-benzenesulfonyl)-amino]-N,N-diethyl-acetamide

생성물 1

HCID 247600902-[(2-Chloro-5-isopropenyl-phenyl)-(3,4-dimethoxy-benzenesulfonyl)-amino]-N,N-diethyl-acetamide수율 38.7%

시약·촉매·용매 2

HCID 142844-(Dimethylamino)pyridine촉매HCID 6344Dichloromethane용매

실험 절차

To a solution of 2-[[2-chloro-5-(1-hydroxy-1-methyl-ethyl)-phenyl]-(3,4-dimethoxy-benzenesulfonyl)-amino]-N,N-diethyl-acetamide (0.527 g, 1 mmol) in DCM (10 mL) was added at 0° C. NEt3 (0.88 mL, 6 eq) and DMAP (7 mg). Methane sulfonylchloride (0.123 mL, 1.5 eq) was added and the mixture warmed to RT and stirred for 6 h. The mixture was partitioned between DCM and water. The aqueous phase was once more extracted with DCM and the combined organic layers dried over MgSO4 and concentrated. The residue was purified by chromatography on SiO2 (hex/EA 1:1, EA, EA/MeOH 9:1) to give the title compound as a colourless solid (0.186 g, 37%). Unreacted starting material (0.29 g, 55%) was also recovered.

후처리

  1. customThe mixture was partitioned between DCM and water
  2. extractionThe aqueous phase was once more extracted with DCM
  3. dry with materialthe combined organic layers dried over MgSO4
  4. concentrationconcentrated
  5. customThe residue was purified by chromatography on SiO2 (hex/EA 1:1, EA, EA/MeOH 9:1)

출처 및 근거

ORD 기록
ord-9b6ee56759ab45e397ef138defd67e09
출처 데이터셋
uspto-grants-2011_08
특허 번호
US08003654B2

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