Potassium Carbonate → Tert-butyl[2-(2-cyclohexyl-ethylsulfanyl)-benzoimidazol-1-yl]-acetate

HRID 2389466Notes

Reaction equation

HRID 2389466 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.C([O-])([O-])=O.[K+].[K+].[CH:25]1([CH2:31][CH2:32]Br)[CH2:30][CH2:29][CH2:28][CH2:27][CH2:26]1>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][CH2:32][CH2:31][CH:25]1[CH2:30][CH2:29][CH2:28][CH2:27][CH2:26]1)([CH3:13])([CH3:14])[CH3:12]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 15440(2-Bromoethyl)cyclohexaneHCID 178451223HCID 178451223, compound

Product 1

HCID 91394306Tert-butyl[2-(2-cyclohexyl-ethylsulfanyl)-benzoimidazol-1-yl]-acetate

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To a suspension of tert-butyl (2-mercapto-benzoimidazol-1-yl)-acetate (Intermediate 3-I, 53 mg, 0.2 mmol) and K2CO3 (41.4 mg, 0.4 mmol) in acetone (0.8 ml) is added 2-cyclohexylethyl bromide (28.8 mg, 22.6 μl). The reaction mixture is kept stirring at reflux for 5 h then filtered on a short plug of silica gel. The solvents are evaporated and the crude is purified by preparative HPLC yielding the title compound in 60% as a colourless oil: tR=7.39 min (LC-1), ESI-MS (pos.): m/z 321.36 [M+H]+; 1H NMR (CDCl3): δ (ppm) 0.80-0.91 (m, 2H), 1.04-1.23 (m, 3H), 1.35 (s, 9H, tBu), 1.35 (m, 1H), 1.54-1.72 (m, 6H), 1.83 (br. s, 1H), 3.32 (t, 2H, SCH2), 4.65 (s, 2H, CH2CO2), 7.07-7.17 (m, 3Harom), 7.61 (m, 1Harom).

Workup

  1. temperatureat reflux for 5 h
  2. filtrationthen filtered on a short plug of silica gel
  3. customThe solvents are evaporated
  4. customthe crude is purified by preparative HPLC

Sources & evidence

ORD record
ord-deab2b3a7e43415992ad2dbd7a042c0a
Source dataset
uspto-grants-2012_09
Patent number
US08273740B2

Reaction notes

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