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

HRID 1719228노트

반응식

HRID 1719228 반응식
[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

참가 물질

6

반응물 3

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

생성물 1

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

시약·촉매·용매 2

HCID 887Methanol용매HCID 962Water용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-810b5162fda84f5b81a03625505b632f
출처 데이터셋
uspto-grants-1985_09
특허 번호
US04539329

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