2,6-Lutidine → 3-(1-Methyl-1-phenyl-ethylcarbamoyl)-benzenesulfonyl chloride

HRID 132079

反応式

HRID 132079 の反応式
[Cl:1][S:2]([C:5]1[CH:6]=[C:7]([CH:11]=[CH:12][CH:13]=1)[C:8](Cl)=[O:9])(=[O:4])=[O:3].[CH3:14][C:15]([NH2:23])([C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)[CH3:16].N1C(C)=CC=CC=1C>C(Cl)Cl.CCOC(C)=O>[CH3:14][C:15]([NH:23][C:8]([C:7]1[CH:6]=[C:5]([S:2]([Cl:1])(=[O:4])=[O:3])[CH:13]=[CH:12][CH:11]=1)=[O:9])([C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)[CH3:16]

参加物

6

反応物 3

HCID 79372,6-LutidineHCID 68509CumylamineHCID 77671Benzoyl chloride, 3-(chlorosulfonyl)-

生成物 1

HCID 597336903-(1-Methyl-1-phenyl-ethylcarbamoyl)-benzenesulfonyl chloride収率 106.7%

試薬・触媒・溶媒 2

HCID 6344Dichloromethane溶媒HCID 8857Ethyl Acetate溶媒

実験手順

3-Chlorosulfonyl-benzoyl chloride (1 g, 4.2 mmol) was dissolved in DCM (10 mL) and cooled in an ice bath. To the solution was added 1-methyl-1-phenyl-ethylamine (0.9 g, 3.8 mmol) and 2,6-lutidine (1 mL, 8.4 mmol). The mixture was allowed to warm up to RT and stirred for 4 h. The reaction mixture was diluted with EtOAc (100 mL) and washed with 1 N HCl (2×75 mL) and brine. The organic layer was dried (MgSO4) and evaporated in vacuo to provide 1.37 g (98%) of 3-(1-methyl-1-phenyl-ethylcarbamoyl)-benzenesulfonyl chloride as a tan solid. 1H-NMR (CDCl3): δ 8.40 (t, 1H, J=1.7 Hz), 8.15-8.18 (m, 2H), 7.72 (t, 1H, J=7.8 Hz), 7.46-7.50 (m, 2H), 7.36-7.41 (m, 2H), 7.27-7.32 (m, 1H), 6.56 (br s, 1H), and 1.87 (s, 6H).

後処理

  1. temperaturecooled in an ice bath
  2. washwashed with 1 N HCl (2×75 mL) and brine
  3. dry with materialThe organic layer was dried (MgSO4)
  4. customevaporated in vacuo

出典と根拠

ORDレコード
ord-0f7bd149a76a4fe7b1d4f8fd802a1eb7
出典データセット
uspto-grants-2008_06
特許番号
US07385066B2

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