Iodine → 2-(4-Iodoethynylphenyl)-3-methyl-1-(1H-1,2,4-triazole-1-yl)butan-2-ol

HRID 64645Notes

Reaction equation

HRID 64645 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][C:6]([C:9]([OH:19])([CH:16]([CH3:18])[CH3:17])[CH2:10][N:11]2[CH:15]=[N:14][CH:13]=[N:12]2)=[CH:5][CH:4]=1)#[CH:2].CO.[I:22]I.[OH-].[Na+]>O>[I:22][C:2]#[C:1][C:3]1[CH:8]=[CH:7][C:6]([C:9]([OH:19])([CH:16]([CH3:17])[CH3:18])[CH2:10][N:11]2[CH:15]=[N:14][CH:13]=[N:12]2)=[CH:5][CH:4]=1

Participants

6

Reactant 4

HCID 807IodineHCID 887MethanolHCID 14798Sodium HydroxideHCID 134736652-(4-ethynylphenyl)-3-methyl-1-(1H-1,2,4-triazole-1-yl)butan-2-ol

Product 1

HCID 134737002-(4-Iodoethynylphenyl)-3-methyl-1-(1H-1,2,4-triazole-1-yl)butan-2-ol

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a solution of 5.1 g 2-(4-ethynylphenyl)-3-methyl-1-(1H-1,2,4-triazole-1-yl)butan-2-ol in 100 ml abs. CH3OH are simultaneously added, with stirring at 20°-25°, 2.6 g iodine and 10 ml 30% NaOH solution. The reaction mixture is maintained at room temperature for 24 hours, with stirring, then poured into 500 ml H2O and extracted with CH2Cl2. The organic phase is washed, dried and evaporated. The residue is stirred in hexane fraction and kept over 16 hours at rest. The precipitate is sucked off and dried to give the title compound m.p. 122° as colourless crystals.

Workup

  1. stirringwith stirring
  2. extractionextracted with CH2Cl2
  3. washThe organic phase is washed
  4. customdried
  5. customevaporated
  6. stirringThe residue is stirred in hexane fraction
  7. customdried

Sources & evidence

ORD record
ord-c31b3b7f96db41958ceae820174652c0
Source dataset
uspto-grants-1986_09
Patent number
US04609668

Reaction notes

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