Sodium hydride → HCID 86735281, compound

HRID 461462

Reaction equation

HRID 461462 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[CH:9]([OH:16])[CH2:10][N:11]1[CH:15]=[CH:14][N:13]=[CH:12]1.[H-].[Na+].Cl[CH2:20][C:21]1[N:22]=[CH:23][S:24][CH:25]=1>O1CCCC1.O>[ClH:1].[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[CH:9]([O:16][CH2:20][C:21]1[N:22]=[CH:23][S:24][CH:25]=1)[CH2:10][N:11]1[CH:15]=[CH:14][N:13]=[CH:12]1

Participants

6

Reactant 3

HCID 24758Sodium hydrideHCID 32238(+-)-alpha-(2,4-Dichlorophenyl)-1H-imidazole-1-ethanolHCID 27632904-(Chloromethyl)-1,3-thiazole2×

Product 1

HCID 86735281HCID 86735281, compoundYield 92.6%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
70 °C

Procedure

A solution of 1-(2,4-dichloro-phenyl)-2-(1-imidazolyl) ethanol (2.4 g, 9.4 mmole) in dry tetrahydrofuran (20 ml) was added to sodium hydride (0.62 g, as an 80% dispersion in oil, 0.02 mole) and warmed at 70° C for 90 minutes. The solution was cooled to 0° C and 4-chloromethylthiazole (1.5 g, 11.2 mmole), dissolved in a little dry tetrahydrofuran, was added. The mixture was stirred at 0° C for 1 hour and at room temperature for 6 hours. Further 4-chloromethylthiazole (0.25 g) was added and the stirring continued for 36 hours. The reaction mixture was then diluted with water (70 ml) and extracted several times with ether. The ether extracts were combined, dried over MgSO4 and evaporated. The oily residue was taken up in dry ether (50 ml) and treated with a solution of HCl in ether. The solid precipitate was collected and recrystallized from a mixture of methanol and di-isopropyl ether to give 1-[2,4-dichloro-β-(4-thiazolylmethoxy) phenethyl]imidazole hydrochloride (1.7 g, 46%) m.p. 183°-184°. (Found: C, 46.3; H, 3.7; N, 10.7. C15H13N3Cl2OS.HCl requires C, 46.1; H, 3.6; N, 10.7%).

Workup

  1. temperatureThe solution was cooled to 0° C
  2. additionwas added
  3. waitthe stirring continued for 36 hours
  4. extractionextracted several times with ether
  5. dry with materialdried over MgSO4
  6. customevaporated
  7. additiontreated with a solution of HCl in ether
  8. customThe solid precipitate was collected
  9. customrecrystallized from a mixture of methanol and di-isopropyl ether

Sources & evidence

ORD record
ord-def45323cb3d433197a0a26f4a50ada9
Source dataset
uspto-grants-1977_12
Patent number
US04062966

Linked notes

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