Water → HCID 20279330, compound

HRID 1248328Notes

Reaction equation

HRID 1248328 reaction equation
S(Cl)([Cl:4])(=O)=O.[Cl:6][C:7]1[CH:8]=[C:9]([CH:27]=[CH:28][C:29]=1[Cl:30])[CH2:10][N:11]1[C:19]2[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=2)[C:13]2([CH2:23][C:22](=[O:24])[NH:21][C:20]2=[O:25])[C:12]1=[O:26].O>C(O)(=O)C>[Cl:4][C:16]1[CH:15]=[C:14]2[C:19](=[CH:18][CH:17]=1)[N:11]([CH2:10][C:9]1[CH:27]=[CH:28][C:29]([Cl:30])=[C:7]([Cl:6])[CH:8]=1)[C:12](=[O:26])[C:13]12[CH2:23][C:22](=[O:24])[NH:21][C:20]1=[O:25]

Participants

5

Reactant 3

HCID 962WaterHCID 24648Sulfuryl chlorideHCID 13691150HCID 13691150, compound

Product 1

HCID 20279330HCID 20279330, compoundYield 58%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
60 °C

Procedure

Sulphuryl chloride (2.74 g.) was added to a stirred suspension of 1'-(3,4-dichlorobenzyl)-spiro[pyrrolidine-3,3'-indoline]-2,2',5-trione (3.0 g.) in acetic acid (50 ml.). The mixture was stirred at 60° C. for 5 hours, cooled to ambient temperature and then stirred at this temperature for 16 hours. The mixture was then poured into water (250 ml.). The white solid which formed was collected by filtration, washed with water, air dried and recrystallised from 2-propanol to give 5'-chloro-1'-(3,4-dichlorobenzyl)-spiro[pyrrolidine-3,3'-indoline]-2,2',5-trione (1.9 g.), m.p. 268°-270° C.

Workup

  1. temperaturecooled to ambient temperature
  2. stirringstirred at this temperature for 16 hours
  3. customThe white solid which formed
  4. filtrationwas collected by filtration
  5. washwashed with water, air
  6. customdried
  7. customrecrystallised from 2-propanol

Sources & evidence

ORD record
ord-842e1b96b29f4707b040771699e89370
Source dataset
uspto-grants-1985_06
Patent number
US04523021

Reaction notes

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