Water → HCID 497093, compound

HRID 1284546Notes

Reaction equation

HRID 1284546 reaction equation
[Cl:1][C:2]1[NH:3][CH:4]=[C:5]([C:8]([O:10][CH2:11][CH3:12])=[O:9])[C:6]=1[Cl:7].[I:13][C:14](=[C:27]([I:29])[I:28])[CH2:15]OS(C1C=CC(C)=CC=1)(=O)=O.C(N(CC)CC)C.O>CN(C)C=O>[I:13][C:14](=[C:27]([I:29])[I:28])[CH2:15][N:3]1[CH:4]=[C:5]([C:8]([O:10][CH2:11][CH3:12])=[O:9])[C:6]([Cl:7])=[C:2]1[Cl:1]

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 132330032,3,3-Triiodoallyl-p-toluenesulfonateHCID 20252102HCID 20252102, compound

Product 1

HCID 497093HCID 497093, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of 104 mg (0.5 mmoles) of 2,3-dichloro-4-ethoxycarbonylpyrrole in 5 ml of dry N,N-dimethylformamide were added 303 mg (0.5 mmoles) of 2,3,3-triiodoallyl-p-toluenesulfonate and 0.07 ml (0.5 mmoles) of triethylamine and the resulting mixture was heated at 60° C. for 2 hours. The reaction mixture was cooled, 10 ml of cold water were added with stirring thereto and the so separated crystalline substance, 1-(2',3',3'-triiodoallyl)-2,3-dichloro-4-ethyoxycarbonylpyrrole, was recovered by filtration, washed with water and then dried. Yield 281 mg (90%), mp 117°-119° C.

Workup

  1. temperatureThe reaction mixture was cooled
  2. filtrationthe so separated crystalline substance, 1-(2',3',3'-triiodoallyl)-2,3-dichloro-4-ethyoxycarbonylpyrrole, was recovered by filtration
  3. washwashed with water
  4. customdried

Sources & evidence

ORD record
ord-d3dc4a754e764a2ba13e91a3629d87c3
Source dataset
uspto-grants-1986_01
Patent number
US04563472

Reaction notes

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