Isopropyl iodide → HCID 58356337, compound

HRID 244675Notes

Reaction equation

HRID 244675 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:3]1[C:4]([C:6]([O:8][CH2:9][CH3:10])=[O:7])=[CH:5][N:1]=[N:2]1)[CH3:20]

Participants

5

Reactant 3

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

Product 1

HCID 58356337HCID 58356337, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
55 °C

Procedure

A mixture of ethyl 2H-1,2,3-triazole-4-carboxylate (1.5 g), potassium carbonate (2.64 g) and 2-iodopropane (1.91 ml) in dry acetonitrile (30 ml) was stirred at 50-60° C. under nitrogen for 2 h. Further 2-iodopropane (0.955 ml) was added and the mixture was stirred at 50-60° C. under nitrogen for 1.5 h. The mixture was cooled to room temperature and allowed to stand for 4 days. The mixture was filtered through a 2 g silica SPE column eluting with ethyl acetate. The solution was concentrated in vacuo, Purification by chromatography on silica gel (100 g cartridge), eluting with a gradient of 0-100% ethyl acetate in cyclohexane over 40 min gave the title compound (315 mg) as a colourless oil.

Workup

  1. stirringthe mixture was stirred at 50-60° C. under nitrogen for 1.5 h
  2. temperatureThe mixture was cooled to room temperature
  3. waitto stand for 4 days
  4. filtrationThe mixture was filtered through a 2 g silica SPE column
  5. washeluting with ethyl acetate
  6. concentrationThe solution was concentrated in vacuo, Purification by chromatography on silica gel (100 g cartridge)
  7. washeluting with a gradient of 0-100% ethyl acetate in cyclohexane over 40 min

Sources & evidence

ORD record
ord-a84413b1b4a44e7bb564e137309053d9
Source dataset
uspto-grants-2014_02
Patent number
US08658635B2

Reaction notes

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