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

HRID 1674664ノート

反応式

HRID 1674664 の反応式
[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]

参加物

6

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 142844-(Dimethylamino)pyridine触媒HCID 6344Dichloromethane溶媒

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-9b6ee56759ab45e397ef138defd67e09
出典データセット
uspto-grants-2011_08
特許番号
US08003654B2

反応ノート

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