Dimethylformamide → Bis-(2-chloroethyl){4-[5-(2-fluorobiphenyl-4-yl)-1,2,4-oxadiazole-3-yl]benzyl}amine

HRID 2407504ノート

反応式

HRID 2407504 の反応式
S(Cl)([Cl:3])=O.[F:5][C:6]1[CH:11]=[C:10]([C:12]2[O:16][N:15]=[C:14]([C:17]3[CH:30]=[CH:29][C:20]([CH2:21][N:22]([CH2:26]CO)[CH2:23][CH2:24]O)=[CH:19][CH:18]=3)[N:13]=2)[CH:9]=[CH:8][C:7]=1[C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1.CN(C)C=O.Cl[CH2:43][Cl:44]>>[Cl:3][CH2:24][CH2:23][N:22]([CH2:26][CH2:43][Cl:44])[CH2:21][C:20]1[CH:29]=[CH:30][C:17]([C:14]2[N:13]=[C:12]([C:10]3[CH:9]=[CH:8][C:7]([C:31]4[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=4)=[C:6]([F:5])[CH:11]=3)[O:16][N:15]=2)=[CH:18][CH:19]=1

参加物

5

反応物 4

HCID 6228DimethylformamideHCID 6344DichloromethaneHCID 24386Thionyl ChlorideHCID 595094342-[{4-[5-(2-Fluorobiphenyl-4-yl)-1,2,4-oxadiazole-3-yl]benzyl}(2-hydroxyethyl)amino]ethanol

生成物 1

HCID 59509478Bis-(2-chloroethyl){4-[5-(2-fluorobiphenyl-4-yl)-1,2,4-oxadiazole-3-yl]benzyl}amine

反応条件

温度
80 °C

実験手順

Thionyl chloride (52 mL, 0.716 mol) is added drop wise to a stirred solution of 2-[{4-[5-(2-fluoro-biphenyl-4-yl)-1,2,4-oxadiazole-3-yl]benzyl}(2-hydroxyethyl)-amino]ethanol (31 g, 0.0715 mol) in dichloromethane (150 mL) at 0° C. N,N-Dimethylformamide (2 mL) is added and the reaction mixture is heated at 80° C. for 1 h. Excess thionyl chloride is removed under reduced pressure and the residue is made alkaline (pH ˜9) by the addition of an aqueous sodium hydroxide solution (4N, 150 mL) at room temperature. The aqueous layer is extracted with ethyl acetate (2×100 mL) and combined organic layers are dried over sodium sulphate. Removal of solvent under reduced pressure gives a viscous liquid, which is purified by column chromatography (silica gel 230-400 mesh, n-hexane:ethyl acetate 7:3) to give bis-(2-chloroethyl){4-[5-(2-fluorobiphenyl-4-yl)-1,2,4-oxadiazole-3-yl]benzyl}amine.

後処理

  1. customExcess thionyl chloride is removed under reduced pressure
  2. additionby the addition of an aqueous sodium hydroxide solution (4N, 150 mL) at room temperature
  3. extractionThe aqueous layer is extracted with ethyl acetate (2×100 mL)
  4. dry with materialare dried over sodium sulphate
  5. customRemoval of solvent under reduced pressure
  6. customgives a viscous liquid, which
  7. customis purified by column chromatography (silica gel 230-400 mesh, n-hexane:ethyl acetate 7:3)

出典と根拠

ORDレコード
ord-04285bb8b1ea4d02a11babda30274159
出典データセット
uspto-grants-2014_08
特許番号
US08809539B2

反応ノート

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