Sodium hydride → HCID 86735282, compound

HRID 461463Notes

Reaction equation

HRID 461463 reaction equation
[Cl:1][C:2]1[S:6][C:5]([CH:7]([OH:14])[CH2:8][N:9]2[CH:13]=[CH:12][N:11]=[CH:10]2)=[CH:4][CH:3]=1.[H-].[Na+].Br[CH2:18][C:19]1[S:20][CH:21]=[CH:22][C:23]=1[Cl:24]>O1CCCC1>[ClH:1].[Cl:1][C:2]1[S:6][C:5]([CH:7]([O:14][CH2:18][C:19]2[S:20][CH:21]=[CH:22][C:23]=2[Cl:24])[CH2:8][N:9]2[CH:13]=[CH:12][N:11]=[CH:10]2)=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 213939252-(Bromomethyl)-3-chlorothiopheneHCID 54114664HCID 54114664, compound

Product 1

HCID 86735282HCID 86735282, compoundYield 52.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Procedure

A solution of 1-(5-chloro-2-thienyl)-2-(1-imidazolyl) ethanol (1.1 g, 4.8 mmole) dissolved in dry tetrahydrofuran (10 ml) was added to a stirred suspension of sodium hydride (0.4 g, as 80% dispersion in oil, 16 mmole) in dry tetrahydrofuran (40 ml). After stirring for 1 hour at room temperature the mixture was cooled in ice and a solution of 2-bromomethyl-3-chloro-thiophene (1.0 g, 4.7 mmole) in dry tetrahydrofuran (10 ml) was added dropwise. The mixture was allowed to stir for a further 1 hour at 15° C and the solvent then removed under vacuum. The residue was extracted several times with diethyl ether and the etheral extracts were combined and evaporated. The residue was taken up in a little diethyl ether and treated with a solution of hydrogen chloride in diethyl ether to precipitate a gum which solidified on trituration with acetone and ether. Recrystallization from a mixture of acetone, methanol and diisopropyl ether gave 1-[2-(5 -chloro-2-thienyl)-2-(3-chloro-2-thienyl methoxy)ethyl]imidazole hydrochloride as a white solid (0.5 g, 32%) m.p. 120°-121° C. (Found: C, 41.6; H, 3.35; N, 6.9. C14H12N2Cl2OS2. HCl requires C, 42.5; H, 3.3; N, 7.1%).

Workup

  1. temperaturewas cooled in ice
  2. stirringto stir for a further 1 hour at 15° C
  3. customthe solvent then removed under vacuum
  4. extractionThe residue was extracted several times with diethyl ether
  5. customevaporated
  6. additiontreated with a solution of hydrogen chloride in diethyl ether
  7. customto precipitate a gum which
  8. customRecrystallization
  9. additionfrom a mixture of acetone, methanol and diisopropyl ether

Sources & evidence

ORD record
ord-43b8f3bcb75b42ba9d2de749df5e3393
Source dataset
uspto-grants-1977_12
Patent number
US04062966

Reaction notes

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