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

HRID 1719228Notes

Reaction equation

HRID 1719228 reaction equation
[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

Participants

6

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-810b5162fda84f5b81a03625505b632f
Source dataset
uspto-grants-1985_09
Patent number
US04539329

Reaction notes

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