Potassium Iodide → HCID 178436205, compound
Reaction equation
[NH2:1][C:2]1[C:10]2[NH:9][C:8]([CH3:11])=[N:7][C:6]=2[CH:5]=[CH:4][CH:3]=1.[CH2:12]([C:14]1[CH:21]=[CH:20][CH:19]=[C:18]([CH3:22])[C:15]=1[CH2:16]Cl)[CH3:13].C(=O)([O-])[O-].[Na+].[Na+].[I-].[K+]>C(COC)OC>[CH2:12]([C:14]1[CH:21]=[CH:20][CH:19]=[C:18]([CH3:22])[C:15]=1[CH2:16][NH:1][C:2]1[C:10]2[NH:9][C:8]([CH3:11])=[N:7][C:6]=2[CH:5]=[CH:4][CH:3]=1)[CH3:13]Participants
Procedure
4-amino-2-methylbenzimidazole (0.4 g, 2.7 mmol) and 2-ethyl-6-methylbenzylchloride (0.46 g, 2.7 mmol) were dissolved in 10 ml dimethoxyethane. Sodium carbonate (0.5 g, 4.7 mmol) and (0.2 g, 4.7 mmol) of potassium iodide were added to the solution. The reaction mixture was refluxed to for 2 h. Inorganic salts were removed by filtration and washed with dimethoxyethane. The filtrate was evaporated to dryness. The residue was purified by column chromatography on silica gel. The product was eluted with a 50:50 mixture of methylene chloride and ethyl acetate. There was obtained 0.21 g of the title compound. (1H-NMR, 400 MHz, CDCl3): 1.1 (t, 3H), 2.35 (s, 3H), 2.45 (s, 3H), 2.70 (q, 2H), 4.35 (s, 2H), 4.45 (bs, 1H), 6.55 (d, 1H), 6.75 (d, 1H), 6.95-7.20 (m, 4H).
Workup
- temperatureThe reaction mixture was refluxed to for 2 h
- customInorganic salts were removed by filtration
- washwashed with dimethoxyethane
- customThe filtrate was evaporated to dryness
- customThe residue was purified by column chromatography on silica gel
- washThe product was eluted with a 50:50 mixture of methylene chloride and ethyl acetate
Sources & evidence
- ORD record
- ord-cea66ba7e60a41dab5fb79c2bf79053c
- Source dataset
- uspto-grants-2002_10
- Patent number
- US06465505B1
Reaction notes
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