Potassium Carbonate → HCID 2129684, compound

HRID 2389502Notes

Reaction equation

HRID 2389502 reaction equation
[CH3:1][C:2]1[CH:11]=[CH:10][C:5]2[NH:6][C:7]([SH:9])=[N:8][C:4]=2[CH:3]=1.Br[CH2:13][CH2:14][O:15][C:16]1[CH:21]=[CH:20][C:19]([Cl:22])=[CH:18][CH:17]=1.C([O-])([O-])=O.[K+].[K+]>CC(C)=O>[Cl:22][C:19]1[CH:20]=[CH:21][C:16]([O:15][CH2:14][CH2:13][S:9][C:7]2[NH:8][C:4]3[CH:3]=[C:2]([CH3:1])[CH:11]=[CH:10][C:5]=3[N:6]=2)=[CH:17][CH:18]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 748541-(2-Bromoethoxy)-4-chlorobenzeneHCID 178423505HCID 178423505, compound

Product 1

HCID 2129684HCID 2129684, compoundYield 55.4%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A suspension of 5-methyl-1H-benzoimidazole-2-thiol (492 mg, 3 mmol), 1-(2-bromo-ethoxy)-4-chloro-benzene (777 mg, 3.3 mmol) and K2CO3 (828 mg, 6 mmol) in acetone (1.0 ml) is refluxed for 3 h. It is cooled down and filtered on filter paper. The solvent is removed in vacuo and the crude purified by flash chromatography on silica-gel (AcOEt/heptane, 3:7), yielding the title compound (530 mg) in 55% as an off-white solid: tR=2.02 min (LC-2), ESI-MS (pos.): m/z 319.21 [M+H]+, ESI-MS (neg.): m/z 317.23 [M−H]+; 1H-NMR (CDCl3): δ (ppm) 2.36 (s, 3H, Me), 3.59 (t, 2H, SCH2), 4.23 (t, 2H, CH2O), 6.75 (d, 2Harom), 6.97 (d, 1Harom), 7.13 (d, 2Harom), 7.18 (s, 1Harom), 7.34 (d, 1Harom).

Workup

  1. temperatureis refluxed for 3 h
  2. temperatureIt is cooled down
  3. filtrationfiltered
  4. filtrationon filter paper
  5. customThe solvent is removed in vacuo
  6. customthe crude purified by flash chromatography on silica-gel (AcOEt/heptane, 3:7)

Sources & evidence

ORD record
ord-5ec2385e89da43ec94a4fddb3f99fbf3
Source dataset
uspto-grants-2012_09
Patent number
US08273740B2

Reaction notes

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