Thionyl Chloride → 3-[6'-Methyl-4'-(4-trifluoromethyl-phenyl)-[2,2']bipyridinyl-6-yl]-benzenesulfonyl chloride

HRID 1927988

反応式

HRID 1927988 の反応式
[CH3:1][C:2]1[N:7]=[C:6]([C:8]2[CH:13]=[CH:12][CH:11]=[C:10]([C:14]3[CH:15]=[C:16]([S:20](O)(=[O:22])=[O:21])[CH:17]=[CH:18][CH:19]=3)[N:9]=2)[CH:5]=[C:4]([C:24]2[CH:29]=[CH:28][C:27]([C:30]([F:33])([F:32])[F:31])=[CH:26][CH:25]=2)[CH:3]=1.S(Cl)([Cl:36])=O.C([O-])(O)=O.[Na+]>CN(C=O)C.CCOC(C)=O>[CH3:1][C:2]1[N:7]=[C:6]([C:8]2[CH:13]=[CH:12][CH:11]=[C:10]([C:14]3[CH:15]=[C:16]([S:20]([Cl:36])(=[O:22])=[O:21])[CH:17]=[CH:18][CH:19]=3)[N:9]=2)[CH:5]=[C:4]([C:24]2[CH:29]=[CH:28][C:27]([C:30]([F:33])([F:32])[F:31])=[CH:26][CH:25]=2)[CH:3]=1

参加物

6

反応物 3

HCID 24386Thionyl Chloride2 回HCID 516892Sodium BicarbonateHCID 167476493-[6'-Methyl-4'-(4-trifluoromethyl-phenyl)-[2,2']bipyridinyl-6-yl]-benzenesulfonic acid

生成物 1

HCID 866154503-[6'-Methyl-4'-(4-trifluoromethyl-phenyl)-[2,2']bipyridinyl-6-yl]-benzenesulfonyl chloride

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide溶媒HCID 8857Ethyl Acetate溶媒

反応条件

温度
23 °C

実験手順

To a suspension of 3-[6′-methyl-4′-(4-trifluoromethyl-phenyl)-[2,2′]bipyridinyl-6-yl]-benzenesulfonic acid (example 345) (2.0 g, 4.25 mmol) in DMF (20 mL) at 23° C. was added thionyl chloride (1.54 mL, 21.25 mmol) and the mixture was stirred at 23° C. for 2 h, then added again SOCl2 (1.54 mL, 21.25 mmol) and the mixture was stirred at 23° C. for 1 h. Diluted with EtOAc, poured into ice cold half-sat. NaHCO3-sol., separated phases, washed organic layer with brine and dried over Na2SO4. Removal of the solvent in vacuum left the title compound as an off-white solid (2.0 g, 98%), which was used without further purification. MS (ISP) 489.2 [(M+H)+] and 491.1 [(M+2+H)+].

後処理

  1. stirringthe mixture was stirred at 23° C. for 1 h
  2. custom, separated phases
  3. washwashed organic layer with brine
  4. dry with materialdried over Na2SO4
  5. customRemoval of the solvent in vacuum
  6. waitleft the title compound as an off-white solid (2.0 g, 98%), which
  7. customwas used without further purification

出典と根拠

ORDレコード
ord-8f7a7879edea4e82bcb626a340b7dc7e
出典データセット
uspto-grants-2012_05
特許番号
US08183262B2

関連ノート

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