Acetonitrile → HCID 70982804, compound

HRID 922602Notes

Reaction equation

HRID 922602 reaction equation
[Cl:1][C:2]1[N:3]=[CH:4][NH:5][C:6]=1[Cl:7].[OH-].[K+].BrCC[C:13]1[C:22]2[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=2)[CH:16]=[CH:15][CH:14]=1.[C:23](#N)[CH3:24]>>[CH2:23]([C:15]1[CH:14]=[CH:13][C:22]2[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=2)[C:16]=1[N:3]1[C:2]([Cl:1])=[C:6]([Cl:7])[N:5]=[CH:4]1)[CH3:24]

Participants

5

Reactant 4

HCID 6342AcetonitrileHCID 14797Potassium HydroxideHCID 1395411-(2-Bromoethyl)naphthaleneHCID 1400184,5-Dichloroimidazole

Product 1

HCID 70982804HCID 70982804, compoundYield 29%

Procedure

4,5-Dichloroimidazole (0.137 g, 1 mmol) was dissolved into 1 mL of acetonitrile. Potassium hydroxide (0.061 g, 1.1 mmol) was added and the mixture was allowed to stir for 0.5 h. 1-(2-bromoethyl)-naphthalene (0.142 mL, 0.235 g, 1 mmol) was added and the solution was allowed to reflux for 2.5 h. The solution was filtered hot to remove a white precipitate (presumed to be KBr) and the solution was allowed to cool to room temperature to yield a tan crystalline material (0.085 g, 29% yield). 1H NMR (500 MHz, DMSO-d6) 8.13 (1H, d, Ar), 7.93 (1H, d, Ar), 7.84 (1H, d, Ar), 7.69 (1H, s, NCHN), 7.58 (2H, m, Ar), 7.42 (1H, t, Ar), 7.27 (1H, d, Ar), 4.31 (2H, t, NCH2), 3.49 (2H, t, CH2). 13C{1H} NMR (125 MHz, DMSO-d6) 135.9 (NCN), 133.4 (Ar—Cl), 133.3 (Ar—Cl), 131.3 (Ar—Cl), 128.6 (Ar—Cl), 127.4 (Ar), 126.9 (Ar), 126.3 (Ar), 125.7 (Ar), 125.5 (Ar), 124.0 (Ar), 123.3 (Ar), 111.9 (Ar), 46.2 (CH2), 32.8 (CH3). MS: m/z=290.04 (theor for C15H12Cl2N2=291.0).

Workup

  1. temperatureto reflux for 2.5 h
  2. filtrationThe solution was filtered hot
  3. customto remove a white precipitate (presumed to be KBr)

Sources & evidence

ORD record
ord-5cd4c92218654cb78ca3bbe495e02d56
Source dataset
uspto-grants-2016_03
Patent number
US09278951B2

Reaction notes

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