Water → HCID 19025800, compound

HRID 1033248Notes

Reaction equation

HRID 1033248 reaction equation
[C:1]1([C:7]2[N:8]=[C:9]([SH:18])[NH:10][C:11]=2[C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.Cl[CH2:20][CH2:21][O:22][CH2:23][CH2:24]Cl.C(=O)([O-])[O-].[K+].[K+].O>[I-].C([N+](CCCC)(CCCC)CCCC)CCC.O1CCCC1>[C:1]1([C:7]2[N:8]=[C:9]([S:18][CH2:20][CH2:21][O:22][CH2:23][CH2:24][S:18][C:9]3[NH:10][C:11]([C:12]4[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=4)=[C:7]([C:1]4[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=4)[N:8]=3)[NH:10][C:11]=2[C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

7

Reactant 4

HCID 962WaterHCID 8115Bis(2-chloroethyl) etherHCID 11430Potassium CarbonateHCID 178527825HCID 178527825, compound

Product 1

HCID 19025800HCID 19025800, compound

Reagents, catalysts & solvents 2

HCID 67553Tetrabutylammonium IodideCatalystHCID 8028TetrahydrofuranSolvent

Procedure

A solution of 4,5-diphenyl-2-mercapto-1H-imidazole (2.63 g, 10.44 mmol), chloroethyl ether (0.6 mL, 5.22 mmol), potassium carbonate (1.59 g, 11.5 mmol) and tetra-n-butylammonium iodide (0.39 g, 1.04 mmol) in tetrahydrofuran (20 mL) was heated to reflux for 14 hours. The solution was cooled, then poured into water (100 mL). This was extracted with methylene chloride (2×100 mL), and the extracts were combined, dried over anhydrous magnesium sulfate, filtered and evaporated. The residue was separated by flash chromatography (3:7 ethyl acetate-hexane, then 1:1 ethyl acetate-hexane) to afford the title product, which was further purified by recrystallization from acetonitrile, mp 232°-234° C. (1.00 g, 1.74 mmol, 33%). 1H NMR (CDCl3): 11.70 (2H, br s); 7.60-7.16 (20H, m); 3.80 (4H, t, J=5.7 Hz); 3.21 (4H, t, J=5.7 Hz). Elemental analysis: calc. C 71.05, H 5.26, N 9.75; obs. C 70.84, H 5.17, N 9.68.

Workup

  1. temperatureto reflux for 14 hours
  2. temperatureThe solution was cooled
  3. extractionThis was extracted with methylene chloride (2×100 mL)
  4. dry with materialdried over anhydrous magnesium sulfate
  5. filtrationfiltered
  6. customevaporated
  7. customThe residue was separated by flash chromatography (3:7 ethyl acetate-hexane

Sources & evidence

ORD record
ord-a6d44ca547604d30a043f19a738ffcac
Source dataset
uspto-grants-1994_05
Patent number
US05310748

Reaction notes

Loading…