Potassium Cyanide → 1'-(4-Bromo-2-fluorobenzyl)-7'-(trifluoromethyl)-spiro[imidazolidine-4,3'-indoline]-2,2',5-trione

HRID 1719228ノート

反応式

HRID 1719228 の反応式
[Br:1][C:2]1[CH:23]=[CH:22][C:5]([CH2:6][N:7]2[C:15]3[C:10](=[CH:11][CH:12]=[CH:13][C:14]=3[C:16]([F:19])([F:18])[F:17])[C:9](=O)[C:8]2=[O:21])=[C:4]([F:24])[CH:3]=1.[C-:25]#[N:26].[K+].[OH2:28].[C:29](=[O:32])([O-])[O-].[NH4+:33].[NH4+]>CO.O>[Br:1][C:2]1[CH:23]=[CH:22][C:5]([CH2:6][N:7]2[C:15]3[C:10](=[CH:11][CH:12]=[CH:13][C:14]=3[C:16]([F:19])([F:17])[F:18])[C:9]3([C:25](=[O:28])[NH:26][C:29](=[O:32])[NH:33]3)[C:8]2=[O:21])=[C:4]([F:24])[CH:3]=1

参加物

6

反応物 3

HCID 9032Potassium CyanideHCID 132512921-(4-Bromo-2-fluorobenzyl)-7-trifluoromethylindoline-2,3-dioneHCID 86740279Ammonium carbonate monohydrate

生成物 1

HCID 132512941'-(4-Bromo-2-fluorobenzyl)-7'-(trifluoromethyl)-spiro[imidazolidine-4,3'-indoline]-2,2',5-trione収率 50.3%

試薬・触媒・溶媒 2

HCID 887Methanol溶媒HCID 962Water溶媒

実験手順

A mixture of 1-(4-bromo-2-fluorobenzyl)-7-trifluoromethylindoline-2,3-dione (3.35 g.), potassium cyanide (1.06 g.) and ammonium carbonate monohydrate (7.8 g.) in methanol (150 ml.) and water (150 ml.) was heated at 45°-50° C. for 16 hours. The reaction mixture was cooled and a slight precipitate removed by filtration. The filtrate was acidified (2M hydrochloric acid, 80 ml.). The solid which formed was washed with water and recrystallised from tetrahydrofuran (THF)/petrol 60-80 to give 1'-(4-bromo-2-fluorobenzyl)-7'-(trifluoromethyl)-spiro[imidazolidine-4,3'-indoline]-2,2',5-trione (A) (1.98 g.), m.p. 197°-199° C.

後処理

  1. temperaturewas heated at 45°-50° C. for 16 hours
  2. temperatureThe reaction mixture was cooled
  3. customa slight precipitate removed by filtration
  4. customThe solid which formed
  5. washwas washed with water
  6. customrecrystallised from tetrahydrofuran (THF)/petrol 60-80

出典と根拠

ORDレコード
ord-810b5162fda84f5b81a03625505b632f
出典データセット
uspto-grants-1985_09
特許番号
US04539329

反応ノート

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