Water → HCID 21083552, compound

HRID 347660Notes

Reaction equation

HRID 347660 reaction equation
Cl[C:2]([O:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)=[O:3].[I:11][C:12]1[CH:13]=[N:14][NH:15][CH:16]=1.C(N(CC)CC)C.O>C(Cl)Cl>[I:11][C:12]1[CH:13]=[N:14][N:15]([C:2]([O:4][C:5]2[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=2)=[O:3])[CH:16]=1

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 15891Phenyl chloroformateHCID 770224-Iodopyrazole

Product 1

HCID 21083552HCID 21083552, compoundYield 95%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Phenyl chloroformate (0.75 mL, 6.0 mmol) is added dropwise to a solution of 4-iodopyrazole (1.05 g, 5.4 mmol) and triethylamine (0.9 mL, 6.5 mmol) in 15 mL CH2Cl2. The reaction is stirred at RT. After 60 h, water is added. The mixture is extracted with CH2Cl2, dried (MgSO4), filtered and concentrated. Hexane is added and the solvent is removed in vacuo. A white solid forms on standing to provide 1.6 g (95%) of phenyl 4-iodo-1H-pyrazole-1-carboxylate. MS (EI) m/z 315.1 (M+).

Workup

  1. extractionThe mixture is extracted with CH2Cl2
  2. dry with materialdried (MgSO4)
  3. filtrationfiltered
  4. concentrationconcentrated
  5. additionHexane is added
  6. customthe solvent is removed in vacuo

Sources & evidence

ORD record
ord-4cc90d1d5c974c55bd1569477e006e4a
Source dataset
uspto-grants-2007_02
Patent number
US07176198B2

Reaction notes

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