Chlorosuccinimide → HCID 54564609, compound

HRID 342750Notes

Reaction equation

HRID 342750 reaction equation
[I-:1].[Cl:2][C:3]1[CH:4]=[C:5]([C:10]2[O:11][C:12](=[CH:17][I:18])[C:13]([CH3:16])([CH3:15])[NH+:14]=2)[CH:6]=[C:7]([Cl:9])[CH:8]=1.ClN1C(=[O:25])CCC1=O>CO.O>[I:1][CH:17]([I:18])[C:12](=[O:11])[C:13]([NH:14][C:10](=[O:25])[C:5]1[CH:4]=[C:3]([Cl:2])[CH:8]=[C:7]([Cl:9])[CH:6]=1)([CH3:16])[CH3:15]

Participants

5

Reactant 2

HCID 31398ChlorosuccinimideHCID 67574234HCID 67574234, compound

Product 1

HCID 54564609HCID 54564609, compoundYield 73.7%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent2×

Procedure

2-(3',5'-dichlorophenyl)-5-iodomethylene-4,4-dimethyloxazolinium iodide (5.0 gm, 0.0098 m) was disolved in methanol (200 ml) and N-chlorosuccinimide (3.3 gm, 0.025 m) was added. The mixture was stirred at room temperature for about 1 hour, then diluted with enough water to obtain a cloudy solution and stirred overnight. The reaction mixture was further diluted with water, then filtered and the solid obtained was dried and recrystallized from a mixture of ethyl acetate and hexane to yield 3.8 gm of the desired product.

Workup

  1. customto obtain a cloudy solution
  2. stirringstirred overnight
  3. filtrationfiltered
  4. customthe solid obtained
  5. customwas dried
  6. customrecrystallized from a mixture of ethyl acetate and hexane

Sources & evidence

ORD record
ord-3b18b50b3d5945f1b2c02db2b691a55d
Source dataset
uspto-grants-1999_01
Patent number
US05859063

Reaction notes

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