Potassium Carbonate → HCID 69313419, compound

HRID 2389503Notes

Reaction equation

HRID 2389503 reaction equation
[C:1]([C:3]1[CH:12]=[CH:11][C:6]2[NH:7][C:8]([SH:10])=[N:9][C:5]=2[CH:4]=1)#[N:2].[CH3:13][O:14][C:15](=[O:24])[C:16]1[CH:21]=[CH:20][CH:19]=[C:18]([CH2:22]Br)[CH:17]=1.C([O-])([O-])=O.[K+].[K+]>CC(C)=O.CN(C=O)C>[C:1]([C:3]1[CH:12]=[CH:11][C:6]2[N:7]=[C:8]([S:10][CH2:22][C:18]3[CH:19]=[CH:20][CH:21]=[C:16]([C:15]([O:14][CH3:13])=[O:24])[CH:17]=3)[NH:9][C:5]=2[CH:4]=1)#[N:2]

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 517981Methyl 3-(bromomethyl)benzoateHCID 178509530HCID 178509530, compound

Product 1

HCID 69313419HCID 69313419, compoundYield 58.8%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideCatalystHCID 180AcetoneSolvent

Procedure

A suspension of 5-cyano-1H-benzoimidazole-2-thiol (35 mg, 0.2 mmol), 3-bromomethyl-benzoic acid methyl ester (46 mg, 0.2 mmol) and K2CO3 (55 mg, 0.4 mmol) in acetone (0.6 ml) and 3 drops of DMF is refluxed for 2 h. It is cooled down and filtered over a short plug of silica gel and rinsed with AcOEt. The solvent is removed under a stream of air. The crude residue is purified by flash chromatography on silica-gel (AcOEt/heptane, 1:2), yielding the title compound (38 mg) in 59% as a yellowish gum: tR=6.14 min (LC-1), ESI-MS (pos.): m/z 324.14 [M+H]+, ESI-MS (neg.): m/z 322.22 [M−H]+; 1H-NMR (CDCl3): δ (ppm) 3.92 (s, 3H, Me), 4.67 (s, 2H, SCH2), 5.29 (s, 1H, NH), 7.36-7.56 (m, 4Harom), 7.65 (d, 1Harom), 7.94 (d, 1Harom), 8.10 (s, 1Harom)

Workup

  1. temperatureis refluxed for 2 h
  2. temperatureIt is cooled down
  3. filtrationfiltered over a short plug of silica gel
  4. washrinsed with AcOEt
  5. customThe solvent is removed under a stream of air
  6. customThe crude residue is purified by flash chromatography on silica-gel (AcOEt/heptane, 1:2)

Sources & evidence

ORD record
ord-debe865882954a46a5d480c8a14be723
Source dataset
uspto-grants-2012_09
Patent number
US08273740B2

Reaction notes

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