Iodine → HCID 178470493, compound

HRID 873807Notes

Reaction equation

HRID 873807 reaction equation
C[N:2]1[CH:6]=[CH:5][C:4]([C:7]([O:9][CH2:10][CH3:11])=[O:8])=[N:3]1.[I:12]I.O=[N+]([O-])[O-].[O-][N+](=O)[O-].[O-][N+](=O)[O-].[O-][N+](=O)[O-].[O-][N+](=O)[O-].[O-][N+](=O)[O-].[Ce+4].[NH4+].[NH4+]>CC#N>[I:12][C:5]1[C:4]([C:7]([O:9][CH2:10][CH3:11])=[O:8])=[N:3][NH:2][CH:6]=1

Participants

5

Reactant 3

HCID 807IodineHCID 180504Ceric ammonium nitrateHCID 10582985ethyl 1-methyl-1H-pyrazole-3-carboxylate

Product 1

HCID 178470493HCID 178470493, compoundYield 166%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
80 °C

Procedure

To a stirred solution of ethyl 1-methyl-1H-pyrazole-3-carboxylate (5 g, 32.4 mmol) in CH3CN (200 mL) under Ar was added I2 (4.94 g, 19.46 mmol) and after 5 min CAN (10.67 g, 19.46 mmol). The reaction mixture was stirred for 1 hr at 80° C., concentrated, quenched with a 10% aq. Na2S2O3 solution, and extracted with CH2Cl2. The combined organic layers were washed with brine, dried over Na2SO4 and evaporated. The crude material was purified by silica gel column chromatography (hexane/EtOAc 25-45%) to afford the title product (9.04 g, 32.3 mmol, 100% yield) as a white solid. tR: 3.78 min (HPLC 1); tR: 0.80 min (LC-MS 2); ESI-MS: 281 [M+H]+ (LC-MS 2); Rf=0.45 (hexane/EtOAc 1:1).

Workup

  1. concentrationconcentrated
  2. customquenched with a 10% aq. Na2S2O3 solution
  3. extractionextracted with CH2Cl2
  4. washThe combined organic layers were washed with brine
  5. dry with materialdried over Na2SO4
  6. customevaporated
  7. customThe crude material was purified by silica gel column chromatography (hexane/EtOAc 25-45%)

Sources & evidence

ORD record
ord-e3da176e44e74702a863f1fbacbe075c
Source dataset
uspto-grants-2015_03
Patent number
US08975417B2

Reaction notes

Loading…