Phosphorus pentachloride → 4-tert-butyl-N-[5-(2-chloro-5-methoxy-phenoxy)-6-chloromethyl-2-(morpholin-4-yl)-pyrimidin-4-yl]-benzenesulphonamide

HRID 37095

反応式

HRID 37095 の反応式
[C:1]([C:5]1[CH:10]=[CH:9][C:8]([S:11]([NH:14][C:15]2[C:20]([O:21][C:22]3[CH:27]=[C:26]([O:28][CH3:29])[CH:25]=[CH:24][C:23]=3[Cl:30])=[C:19]([CH2:31]O)[N:18]=[C:17]([N:33]3[CH2:38][CH2:37][O:36][CH2:35][CH2:34]3)[N:16]=2)(=[O:13])=[O:12])=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2].P(Cl)(Cl)(Cl)(Cl)[Cl:40]>O=P(Cl)(Cl)Cl>[C:1]([C:5]1[CH:6]=[CH:7][C:8]([S:11]([NH:14][C:15]2[C:20]([O:21][C:22]3[CH:27]=[C:26]([O:28][CH3:29])[CH:25]=[CH:24][C:23]=3[Cl:30])=[C:19]([CH2:31][Cl:40])[N:18]=[C:17]([N:33]3[CH2:34][CH2:35][O:36][CH2:37][CH2:38]3)[N:16]=2)(=[O:12])=[O:13])=[CH:9][CH:10]=1)([CH3:2])([CH3:4])[CH3:3]

参加物

4

反応物 2

HCID 24819Phosphorus pentachlorideHCID 199347574-tert-butyl-N-[5-(2-chloro-5-methoxy-phenoxy)-6-hydroxymethyl-2-(morpholin-4-yl)-pyrimidin-4-yl]-benzenesulphonamide

生成物 1

HCID 199347554-tert-butyl-N-[5-(2-chloro-5-methoxy-phenoxy)-6-chloromethyl-2-(morpholin-4-yl)-pyrimidin-4-yl]-benzenesulphonamide収率 63.8%

試薬・触媒・溶媒 1

HCID 24813Phosphorus oxychloride溶媒

実験手順

4.57 g of 4-tert-butyl-N-[5-(2-chloro-5-methoxy-phenoxy)-6-hydroxymethyl-2-(morpholin-4-yl)-pyrimidin-4-yl]benzenesulphonamide in 50 ml of POCl3 were stirred with 2.03 g of PCl5 at 20° C. for 2 hours. Thereafter, the POCl3 was distilled off and the residue was partitioned between ethyl acetate and aqueous 1N NaOH. The organic phase was washed with water, dried and the solvent was evaporated. The residue was chromatographed over silica gel with dichloromethane and chloroform, thereafter recrystallized from dichloromethane-ethanol. There were obtained 3.01 g of 4-tert-butyl-N-[5-(2-chloro-5-methoxy-phenoxy)-6-chloromethyl-2-(morpholin-4-yl)-pyrimidin-4-yl]-benzenesulphonamide, m.p. 170° C., MS: M=581.

後処理

  1. distillationThereafter, the POCl3 was distilled off
  2. customthe residue was partitioned between ethyl acetate and aqueous 1N NaOH
  3. washThe organic phase was washed with water
  4. customdried
  5. customthe solvent was evaporated
  6. customThe residue was chromatographed over silica gel with dichloromethane and chloroform
  7. customrecrystallized from dichloromethane-ethanol

出典と根拠

ORDレコード
ord-fc184ab77cc448dcb117f42007e8a033
出典データセット
uspto-grants-1995_05
特許番号
US05420129

関連ノート

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