Water → HCID 86614870, compound

HRID 549485Notes

Reaction equation

HRID 549485 reaction equation
[NH:1]1[C:5]2[C:6]3[C:11]([C:12]4[CH:13]=[CH:14][CH:15]=[CH:16][C:17]=4[C:4]=2[N:3]=[C:2]1[C:18]1[C:25]([C:26]#[N:27])=[CH:24][CH:23]=[CH:22][C:19]=1[C:20]#[N:21])=[CH:10][CH:9]=[CH:8][CH:7]=3.C(=O)([O-])[O-].[Cs+].[Cs+].O.C(OCC)(=O)C.[Cl:41][CH2:42]I>>[Cl:41][CH2:42][N:1]1[C:5]2[C:6]3[C:11]([C:12]4[CH:13]=[CH:14][CH:15]=[CH:16][C:17]=4[C:4]=2[N:3]=[C:2]1[C:18]1[C:25]([C:26]#[N:27])=[CH:24][CH:23]=[CH:22][C:19]=1[C:20]#[N:21])=[CH:10][CH:9]=[CH:8][CH:7]=3

Participants

6

Reactant 5

HCID 962WaterHCID 8857Ethyl AcetateHCID 10796Cesium carbonateHCID 11644ChloroiodomethaneHCID 11508436HCID 11508436, compound

Product 1

HCID 86614870HCID 86614870, compoundYield 31%

Conditions

Temperature
80 °C

Procedure

2-(1H-phenanthro[9,10-d]imidazol-2-yl)isophthalonitrile from Step 2 (1 g, 2.91 mmol) was mixed with cesium carbonate (1.14 g, 3.49 mmol) in chloroiodomethane (10 mL). The mixture was heated to 80° C. overnight. The reaction was cooled to room temperature and poured into 200 mL water and 500 mL ethyl acetate. The layers were separated, and the organic layer was washed with 200 mL water, 200 mL saturated aqueous sodium bicarbonate solution, 100 mL brine, and dried over anhydrous magnesium sulfate. The solvent was removed under reduced pressure. The crude solid was purified by flash column chromatography using 40% ethyl acetate in hexane to give 357 mg of 2-[1-(chloromethyl)-1H-phenanthro[9,10-d]imidazol-2-yl]isophthalonitrile (31%) plus 650 mg of a mixture of product and starting material.

Workup

  1. temperatureThe reaction was cooled to room temperature
  2. customThe layers were separated
  3. washthe organic layer was washed with 200 mL water, 200 mL saturated aqueous sodium bicarbonate solution, 100 mL brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customThe solvent was removed under reduced pressure
  6. customThe crude solid was purified by flash column chromatography

Sources & evidence

ORD record
ord-9de81bc47fb94dd4ba97ba363d2f8ad1
Source dataset
uspto-grants-2011_05
Patent number
US07943649B2

Reaction notes

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