Water → HCID 20501036, compound

HRID 851767Notes

Reaction equation

HRID 851767 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:22]=[CH:23][C:24]=1[Cl:25])[CH2:5][N:6]1[C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[C:8]2([C:18](=[O:19])[NH:17][C:16](=[O:20])[NH:15]2)[C:7]1=[O:21].P(Cl)(Cl)(Cl)=O.O.CN(C)[CH:34]=[O:35]>>[Cl:1][C:2]1[CH:3]=[C:4]([CH:22]=[CH:23][C:24]=1[Cl:25])[CH2:5][N:6]1[C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[C:8]2([C:18](=[O:19])[NH:17][C:16](=[O:20])[N:15]2[CH:34]=[O:35])[C:7]1=[O:21]

Participants

5

Reactant 4

HCID 962WaterHCID 6228DimethylformamideHCID 24813Phosphorus oxychlorideHCID 13564624HCID 13564624, compound

Product 1

HCID 20501036HCID 20501036, compound

Conditions

Temperature
60 °C

Procedure

1'-(3,4-Dichlorobenzyl)-spiro[imidazolidine-4,3'-indoline]-2,2',5-trione (1.8 g.) was added to a solution of phosphorus oxychloride (0.55 ml.) in N,N-dimethylformamide (20 ml.) and the mixture was stirred at 60° C. for 90 minutes. The solution obtained was then poured into water (150 ml.). The solid which formed was collected by filtration, washed with water, air-dried and then recrystallised twice from ethyl acetate/petrol 60-80 to give 1'-(3,4-dichlorobenzyl)-3-formyl-spiro[imidazolidine-4,3'-indoline]-2,2',5-trione (0.6 g.), m.p. 244°-46° C.

Workup

  1. customThe solution obtained
  2. customThe solid which formed
  3. filtrationwas collected by filtration
  4. washwashed with water
  5. customair-dried
  6. customrecrystallised twice from ethyl acetate/petrol 60-80

Sources & evidence

ORD record
ord-e8ebe39458b94adba1bbe5e7f3b5b41e
Source dataset
uspto-grants-1983_05
Patent number
US04386100

Reaction notes

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