Water → HCID 86614870, compound

HRID 2117985Notes

Reaction equation

HRID 2117985 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 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 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-6d6d28e8f3f14aae8e89d5875bf67d1e
Source dataset
uspto-grants-2008_10
Patent number
US07442716B2

Reaction notes

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