Iodine → 2-(3-Chloro-5-trifluoromethyl-2-pyridylazo)-5-(diethylamino)phenol

HRID 1266935Notes

Reaction equation

HRID 1266935 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:26][NH2:27])=[N:18][CH:19]=[C:20]([C:22]([F:25])([F:24])[F:23])[CH:21]=1.O.OO>O.C(O)(=O)C.CN(C)C=O>[Cl:15][C:16]1[C:17]([N:26]=[N:27][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]([C:22]([F:25])([F:23])[F:24])[CH:21]=1

Participants

8

Reactant 4

HCID 807IodineHCID 70623-(Diethylamino)phenolHCID 449047Hydrogen peroxide waterHCID 12726913-Chloro-2-hydrazinyl-5-(trifluoromethyl)pyridine

Product 1

HCID 1357185412-(3-Chloro-5-trifluoromethyl-2-pyridylazo)-5-(diethylamino)phenol

Reagents, catalysts & solvents 3

HCID 176Acetic AcidSolventHCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

Next, a reaction flask was loaded with 3-(N,N-diethlyamino)phenol (1.3 g), dimethylformamide (9 ml), acetic acid (3 ml) and iodine (0.14 g), and they were mixed, followed by addition of 3-chloro-2-hydrazino-5-trifluoromethylpyridine (1.0 g) to the flask with stirring. Then, to this mixture, a 30 % hydrogen peroxide water (1.4 g) was dropwise added in one hour and the mixture was stirred overnight. Water was added to this reaction mixture, followed by extraction with ether. The organic layer was condensed to precipitate crystals. The crystals were filtrated for collection and dried to give intended crystals (0.5 g).

Workup

  1. additionwere mixed
  2. stirringthe mixture was stirred overnight
  3. extractionfollowed by extraction with ether
  4. customcondensed
  5. customto precipitate crystals
  6. filtrationThe crystals were filtrated for collection
  7. customdried
  8. customto give

Sources & evidence

ORD record
ord-788a0bf45c3c4b77a024d21a42edf4dd
Source dataset
uspto-grants-2003_04
Patent number
US06551682B1

Reaction notes

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