Hydrochloric Acid → HCID 20501027, compound

HRID 851775Notes

Reaction equation

HRID 851775 reaction equation
[OH-].[K+].[Br:3][C:4]1[CH:26]=[CH:25][C:7]([CH2:8][N:9]2[C:17]3[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=3)[C:11]3([C:21](=[O:22])[NH:20][C:19](=[O:23])[NH:18]3)[C:10]2=[O:24])=[C:6]([F:27])[CH:5]=1.[C:28]([O:34][CH2:35]Cl)(=[O:33])[C:29]([CH3:32])([CH3:31])[CH3:30].Cl>CS(C)=O.O>[Br:3][C:4]1[CH:26]=[CH:25][C:7]([CH2:8][N:9]2[C:17]3[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=3)[C:11]3([C:21](=[O:22])[N:20]([CH2:35][O:34][C:28](=[O:33])[C:29]([CH3:32])([CH3:31])[CH3:30])[C:19](=[O:23])[NH:18]3)[C:10]2=[O:24])=[C:6]([F:27])[CH:5]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 14797Potassium HydroxideHCID 87885Chloromethyl pivalateHCID 20434016HCID 20434016, compound

Product 1

HCID 20501027HCID 20501027, compound

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolvent

Procedure

Ethanolic potassium hydroxide solution (1 M; 5.2 ml) was added to a solution of 1'-(4-bromo-2-fluorobenzyl)-spiro-[imidazolidine-4,3'-indoline]-2,2',5-trione (2.0 g.) in dimethyl sulphoxide (10 ml.). The solution was stirred for 5 minutes and then chloromethyl pivalate (0.75 g.) was slowly added. After the addition was completed, the reaction mixture was further stirred for 16 hours; and then poured into water (100 ml.). The aqueous mixture was carefully acidified (concentrated hydrochloric acid). The precipitate which formed was washed with water, air dried and recrystallised twice from 2-propanol to give 1'-(4-bromo-2-fluorobenzyl)-1-(pivaloyloxymethyl)-spiro[imidazolidine-4,3'-indoline]-2,2',5-trione, as a white solid (0.75 g.), m.p. 220°-222° C.

Workup

  1. additionAfter the addition
  2. stirringthe reaction mixture was further stirred for 16 hours
  3. customThe precipitate which formed
  4. washwas washed with water, air
  5. customdried
  6. customrecrystallised twice from 2-propanol

Sources & evidence

ORD record
ord-64269938a1db41f98ad6ac7e1fa6cad4
Source dataset
uspto-grants-1983_05
Patent number
US04386100

Reaction notes

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