Water → HCID 20434024, compound

HRID 851762Notes

Reaction equation

HRID 851762 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([C:23](=[O:24])[NH:22][C:21](=[O:25])[NH:20]2)[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[C:23](=[O:24])[NH:22][C:21](=[O:25])[NH:20]1

Participants

5

Reactant 3

HCID 962WaterHCID 24648Sulfuryl chlorideHCID 13564624HCID 13564624, compound

Product 1

HCID 20434024HCID 20434024, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

Sulphuryl chloride (16.0 ml.) was added during 10 minutes to a stirred mixture of 1'-(3,4-dichlorobenzyl)-spiro[imidazolidine-4,3'-indoline]-2,2',5-trione (28.2 g.) in acetic acid (400 ml.). The mixture obtained was then stirred at 60°-65° C. for 40 minutes. The clear solution which formed was poured into water (3 l.). The solid which was precipitated was collected by filtration, washed with water and air-dried. Recrystallisation of the crude solid thus obtained from aqueous propan-2-ol gave 5'-chloro-1'-(3,4-dichlorobenzyl)-spiro[imidazolidine-4,3'-indoline]-2,2',5-trione (15.4 g.), m.p. 257°-259° C.

Workup

  1. customThe mixture obtained
  2. customThe clear solution which formed
  3. customThe solid which was precipitated
  4. filtrationwas collected by filtration
  5. washwashed with water
  6. customair-dried
  7. customRecrystallisation of the crude solid
  8. customthus obtained from aqueous propan-2-ol

Sources & evidence

ORD record
ord-8e1904d61f294c9f85166b037c51643e
Source dataset
uspto-grants-1983_05
Patent number
US04386100

Reaction notes

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