Iodine → Ethyl 4-iodo-1,3-dimethyl-1H-pyrazole-5-carboxylate

HRID 1463309Notes

Reaction equation

HRID 1463309 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[N:10]([CH3:11])[N:9]=[C:8]([CH3:12])[CH:7]=1)=[O:5])[CH3:2].[I:13]I.O.S(=O)(O)[O-].[Na+]>CC([O-])=O.ClCCCl>[CH2:1]([O:3][C:4]([C:6]1[N:10]([CH3:11])[N:9]=[C:8]([CH3:12])[C:7]=1[I:13])=[O:5])[CH3:2]

Participants

7

Reactant 4

HCID 807IodineHCID 962WaterHCID 1385761,3-Dimethyl-5-ethoxycarbonylpyrazoleHCID 23665763Sodium Bisulfite

Product 1

HCID 57269596Ethyl 4-iodo-1,3-dimethyl-1H-pyrazole-5-carboxylate

Reagents, catalysts & solvents 2

HCID 111,2-DichloroethaneSolventHCID 175AcetateSolvent

Procedure

1,3-Dimethyl-5-pyrazolcarboxylic acid ethyl ester (185 g, 1.1 mol), iodine (140 g, 0.55 mol) and HIO3 (38.7 g, 0.22 mol) are heated, under reflux, in acetic acid glacial (450 ml), water (150 ml) and 1,2-dichloroethane (150 ml) for 1.5 hours. The mixture is discoloured with saturated sodium bisulfite, evaporated under reduced pressure and the product extracted with ether. The organic phase is washed with sodium bisulfite and aqueous sodium bicarbonate solution.

Workup

  1. customevaporated under reduced pressure
  2. extractionthe product extracted with ether
  3. washThe organic phase is washed with sodium bisulfite and aqueous sodium bicarbonate solution

Sources & evidence

ORD record
ord-9df71c6ae535483b9cb4e6ee3896f696
Source dataset
uspto-grants-1994_04
Patent number
US05300521

Reaction notes

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