Iodine → HCID 14599974, compound

HRID 1110962Notes

Reaction equation

HRID 1110962 reaction equation
[CH3:1][O:2][C:3]1[CH:17]=[CH:16][CH:15]=[CH:14][C:4]=1[C:5]([C:7]1[NH:8][C:9]([Cl:13])=[C:10]([Cl:12])[CH:11]=1)=[O:6].[OH-].[Na+].N1C=CC=C1.[I:25]I.[I-].[Na+].S([O-])([O-])(=O)=S.[Na+].[Na+]>O.O1CCOCC1>[CH3:1][O:2][C:3]1[CH:17]=[CH:16][CH:15]=[CH:14][C:4]=1[C:5]([C:7]1[NH:8][C:9]([Cl:13])=[C:10]([Cl:12])[C:11]=1[I:25])=[O:6]

Participants

9

Reactant 6

HCID 807IodineHCID 5238Sodium IodideHCID 8027PyrroleHCID 14798Sodium HydroxideHCID 24477Sodium ThiosulfateHCID 14599973HCID 14599973, compound

Product 1

HCID 14599974HCID 14599974, compoundYield 78.3%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Procedure

Added to 1.08 g of 2-(2-methoxybenzoyl)-4,5-dichloropyrrole were 16 ml of a 1:1 mixture of dioxane and water and 4 ml of a 1 N aqueous solution of sodium hydroxide to dissolve the pyrrole derivative, followed by the addition of 12 ml of an aqueous solution containing 1.2 g of iodine and 1.44 g of sodium iodide. The resultant mixture was stirred at room temperature for 15 hours. Thereafter, 40 ml of a 1 N aqueous solution of sodium thiosulfate was added, followed by stirring for 1 hour. Crystals thus deposited were collected by filtration, washed with water and then dried to obtain 1.24 g of 2-(2-methoxybenzoyl)-3-iodo-4,5-dichloropyrrole (Compound No. 1).

Workup

  1. filtrationCrystals thus deposited were collected by filtration
  2. washwashed with water
  3. customdried

Sources & evidence

ORD record
ord-e2d9834b715c421f97d40a6ccdcad060
Source dataset
uspto-grants-1990_12
Patent number
US04977275

Reaction notes

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