Water → 1H-Pyrrole, 2,3-dichloro-4-nitro-1-(2,3,3-triiodo-2-propenyl)-

HRID 1284544Notes

Reaction equation

HRID 1284544 reaction equation
[Cl:1][C:2]1[NH:3][CH:4]=[C:5]([N+:8]([O-:10])=[O:9])[C:6]=1[Cl:7].[I:11][C:12](=[C:25]([I:27])[I:26])[CH2:13]OS(C1C=CC(C)=CC=1)(=O)=O.C(N(CC)CC)C.O>CN(C)C=O>[I:11][C:12](=[C:25]([I:27])[I:26])[CH2:13][N:3]1[CH:4]=[C:5]([N+:8]([O-:10])=[O:9])[C:6]([Cl:7])=[C:2]1[Cl:1]

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 133275Pyrrolomycin AHCID 132330032,3,3-Triiodoallyl-p-toluenesulfonate

Product 1

HCID 4970871H-Pyrrole, 2,3-dichloro-4-nitro-1-(2,3,3-triiodo-2-propenyl)-

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of 220 mg (1.2 mmoles) of 2,3-dichloro-4-nitropyrrole (pyrrolomycin A) in 10 ml of dry N,N-dimethylformamide were added 606 ml (1 mmole) of 2,3,3-triiodoallyl-p-toluenesulfonate and 0.14 ml (1 mmole) of triethylamine and the resulting mixture was heated at 60° C. for 30 minutes. After cooling, 20 ml of cold water were added dropwise with stirring to the reaction mixture and stirring was continued for a further one hour. The so separated crystalline substance, 1-(2',3',3'-triiodoallyl)-2,3-dichloro-4-nitropyrrole, was recovered by filtration, washed with water and then dried. Yield 567 mg (95%), mp 126°-127° C.

Workup

  1. temperatureAfter cooling
  2. stirringstirring
  3. customThe so separated crystalline substance, 1-(2',3',3'-triiodoallyl)-2,3-dichloro-4-nitropyrrole
  4. filtrationwas recovered by filtration
  5. washwashed with water
  6. customdried

Sources & evidence

ORD record
ord-b69a3e6e205c4d089f45258737129aca
Source dataset
uspto-grants-1986_01
Patent number
US04563472

Reaction notes

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