Iodine → 110518-93-9

HRID 1266937Notes

Reaction equation

HRID 1266937 reaction equation
[CH2:1]([N:3]([C:6]1[CH:7]=[C:8]([OH:12])[CH:9]=[CH:10][CH:11]=1)[CH2:4][CH3:5])[CH3:2].II.[Cl:15][C:16]1[C:17]([NH:23][NH2:24])=[N:18][CH:19]=[C:20]([Cl:22])[CH:21]=1.O.OO>C(O)(=O)C.CN(C)C=O>[Cl:15][C:16]1[C:17]([N:23]=[N:24][C:9]2[CH:10]=[CH:11][C:6]([N:3]([CH2:4][CH3:5])[CH2:1][CH3:2])=[CH:7][C:8]=2[OH:12])=[N:18][CH:19]=[C:20]([Cl:22])[CH:21]=1

Participants

7

Reactant 4

HCID 807IodineHCID 70623-(Diethylamino)phenolHCID 449047Hydrogen peroxide waterHCID 6009663,5-Dichloro-2-hydrazinylpyridine

Product 1

HCID 135754683110518-93-9

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 6228DimethylformamideSolvent

Procedure

Next, a flask was loaded with 3-(N,N-diethylamino)phenol (1.7 g), dimethylformamide (14 ml), acetic acid (5 ml) and iodine (0.24 g), and they were mixed, followed by addition of 3,5-dichloro-2-hydrazinopyridine (1.6 g) to the flask with stirring. Then, to this, a 30% hydrogen peroxide water (2.4 g) was dropwise added in 90 minutes and the mixture was stirred overnight. The reaction mixture was filtrated, and ether and water were added to the filtrate, followed by stirring. After stirring, the ether layer was collected and condensed to precipitate crystals. The crystals were filtrated for collection and dried to give intended crystals (0.54 g).

Workup

  1. additionwere mixed
  2. stirringthe mixture was stirred overnight
  3. filtrationThe reaction mixture was filtrated
  4. additionether and water were added to the filtrate
  5. stirringby stirring
  6. stirringAfter stirring
  7. customthe ether layer was collected
  8. customcondensed
  9. customto precipitate crystals
  10. filtrationThe crystals were filtrated for collection
  11. customdried
  12. customto give

Sources & evidence

ORD record
ord-77ce6ef7446e417c99d13f113c953862
Source dataset
uspto-grants-2003_04
Patent number
US06551682B1

Reaction notes

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