Potassium Carbonate → HCID 90961260, compound

HRID 2389480Notes

Reaction equation

HRID 2389480 reaction equation
[SH:1][C:2]1[N:6]([CH2:7][C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])[C:5]2[CH:15]=[CH:16][CH:17]=[CH:18][C:4]=2[N:3]=1.[CH3:19][O:20][C:21](=[O:30])[C:22]1[CH:27]=[CH:26][CH:25]=[C:24]([CH2:28]Br)[CH:23]=1.C([O-])([O-])=O.[K+].[K+]>CC(C)=O>[C:11]([O:10][C:8](=[O:9])[CH2:7][N:6]1[C:5]2[CH:15]=[CH:16][CH:17]=[CH:18][C:4]=2[N:3]=[C:2]1[S:1][CH2:28][C:24]1[CH:25]=[CH:26][CH:27]=[C:22]([C:21]([O:20][CH3:19])=[O:30])[CH:23]=1)([CH3:13])([CH3:14])[CH3:12]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 517981Methyl 3-(bromomethyl)benzoateHCID 178451223HCID 178451223, compound

Product 1

HCID 90961260HCID 90961260, compoundYield 75.2%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A mixture of tert-butyl (2-mercapto-benzoimidazol-1-yl)-acetate (Intermediate 3-1,264 mg, 1 mmol), 3-bromomethyl-benzoic acid methyl ester (252 mg, 1.1 mmol) and K2CO3 (276 mg, 2 mmol) in acetone (4 ml) is allowed to stir at rt for 2.5 h. The suspension is cooled down to rt and filtered on a funnel filled with cotton wool. Evaporation of the solvent in vacuo affords a residue that is purified by flash-chromatography on silica-gel (AcOEt/heptane, 1:3), yielding the title compound (310 mg) in 75% as a colourless syrup: tR=7.19 min (LC-1), ESI-MS (pos.): m/z 413.3 [M+H]+; 1H-NMR (CDCl3): δ (ppm) 1.42 (s, 9H, tBu), 3.92 (s, 3H, OMe), 4.65 (s, 2H), 4.69 (s, 1H), 7.19-7.26 (m, 3Harom), 7.36 (t, 1Harom), 7.59 (d, 1Harom), 7.73 (m, 1 Harom), 7.92 (d, 1Harom), 8.06 (s, 1Harom).

Workup

  1. temperatureThe suspension is cooled down to rt
  2. filtrationfiltered on a funnel
  3. additionfilled with cotton wool
  4. customEvaporation of the solvent in vacuo
  5. customaffords a residue that
  6. customis purified by flash-chromatography on silica-gel (AcOEt/heptane, 1:3)

Sources & evidence

ORD record
ord-7d2e8db231974f12ace4826dac537fb8
Source dataset
uspto-grants-2012_09
Patent number
US08273740B2

Reaction notes

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