Bis(2-chloroethyl) ether → HCID 86723141, compound

HRID 868849Notes

Reaction equation

HRID 868849 reaction equation
C(=O)([O-])[O-].[K+].[K+].[I:7][C:8]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[NH:10][N:9]=1.[Cl:17][CH2:18][CH2:19][O:20][CH2:21][CH2:22]Cl>C(#N)C>[Cl:17][CH2:18][CH2:19][O:20][CH2:21][CH2:22][N:10]1[C:11]2[C:16](=[CH:15][CH:14]=[CH:13][CH:12]=2)[C:8]([I:7])=[N:9]1

Participants

5

Reactant 3

HCID 8115Bis(2-chloroethyl) etherHCID 11430Potassium CarbonateHCID 178506566HCID 178506566, compound

Product 1

HCID 86723141HCID 86723141, compoundYield 56%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Potassium carbonate (1.1 g, 8.2 mmol) was added to a solution of 3-iodoindazole (1.0 g, 4.1 mmol) and bis(2-chloroethyl)ether (1.5 g, 10.3 mmol) in ACN (20 mL) at rt. The reaction was heated to reflux overnight, and the filtered and concentrated. The residue was purified by silica gel chromatography to give 800 mg (56%) of the title compound as a yellow oil. 1H NMR (400 MHz, CDCl3): δ 3.47 (2H, t, J=5.6 Hz), 3.60 (2H, t, J=5.6 Hz), 3.94 (2H, t, J=5.2 Hz), 4.58 (2H, t, J=5.6 Hz), 7.20 (1H, t, J=7.6 Hz), 7.41-7.49 (3H, m). The minor isomer was not isolated or characterized.

Workup

  1. temperatureThe reaction was heated
  2. temperatureto reflux overnight
  3. filtrationthe filtered
  4. concentrationconcentrated
  5. customThe residue was purified by silica gel chromatography

Sources & evidence

ORD record
ord-00cac48d64d74c6f9e69c94d127cbacf
Source dataset
uspto-grants-2015_03
Patent number
US08969343B2

Reaction notes

Loading…