Isopropyl iodide → HCID 58356328, compound

HRID 244664Notes

Reaction equation

HRID 244664 reaction equation
[N:1]1[NH:2][N:3]=[C:4]([C:6]([O:8][CH2:9][CH3:10])=[O:7])[CH:5]=1.C(=O)([O-])[O-].[K+].[K+].I[CH:18]([CH3:20])[CH3:19]>C(#N)C>[CH3:19][CH:18]([N:2]1[N:3]=[C:4]([C:6]([O:8][CH2:9][CH3:10])=[O:7])[CH:5]=[N:1]1)[CH3:20]

Participants

5

Reactant 3

HCID 6362Isopropyl iodide2×HCID 11430Potassium CarbonateHCID 6419107ethyl 1H-1,2,3-triazole-4-carboxylate

Product 1

HCID 58356328HCID 58356328, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
55 °C

Procedure

A mixture of ethyl 2H-1,2,3-triazole-4-carboxylate (1 g), potassium carbonate (1.76 g) and 2-iodopropane (1.27 ml) in dry acetonitrile (20 ml) was stirred at 50-60° C. under nitrogen for 2 h. Further 2-iodopropane (0.70 ml) was added and the mixture stirred at 50-60° C. under nitrogen for 16 h. After cooling to room temperature, the mixture was filtered through a 2 g SPE-Silica column with ethyl acetate and the filtrate concentrated in vacuo, Purification of the residue by chromatography on silica gel (70 g silica cartridge), eluting with a gradient of 0-25% ethyl acetate in cyclohexane over 40 min gave the title compound (670 mg) as a colourless oil.

Workup

  1. stirringthe mixture stirred at 50-60° C. under nitrogen for 16 h
  2. temperatureAfter cooling to room temperature
  3. filtrationthe mixture was filtered through a 2 g SPE-Silica column with ethyl acetate
  4. concentrationthe filtrate concentrated in vacuo, Purification of the residue by chromatography on silica gel (70 g silica cartridge)
  5. washeluting with a gradient of 0-25% ethyl acetate in cyclohexane over 40 min

Sources & evidence

ORD record
ord-b89a1f9d5092415f87507a5144cb08a1
Source dataset
uspto-grants-2014_02
Patent number
US08658635B2

Reaction notes

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