Imidazole → HCID 20389856, compound

HRID 426771Notes

Reaction equation

HRID 426771 reaction equation
[NH:1]1[CH:5]=[CH:4][N:3]=[CH:2]1.[Na].[H][H].Br[CH2:10][C:11]1[C:23]2[CH:22]=[CH:21][S:20][C:19]=2[C:18]2[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=2)[CH:12]=1>O1CCCC1>[S:20]1[CH:21]=[CH:22][C:23]2[C:11]([CH2:10][N:1]3[CH:5]=[CH:4][N:3]=[CH:2]3)=[CH:12][C:13]3[C:18]([C:19]1=2)=[CH:17][CH:16]=[CH:15][CH:14]=3

Participants

6

Reactant 4

HCID 795ImidazoleHCID 5360545Sodium2×HCID 20389838HCID 20389838, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 20389856HCID 20389856, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

13.6 g (0.2 mole) of 1H-imidazole is dissolved in 200 ml of absolute tetrahydrofuran, and to the solution is added portionwise with stirring, in a nitrogen atmosphere, 2.3 g (0.1 gram atom) of sodium, with slight self-heating occurring accompanied by the evolution of hydrogen. The reaction mixture is heated at 45°-50° until the sodium has been completely absorbed. There is subsequently added dropwise at the same temperature, within 60 minutes, a solution of 27.7 g (0.1 mole) of 4-(bromomethyl)-naphtho[1,2-b]thiophene in 50 ml of tetrahydrofuran, and stirring is continued at 45°-50° for a further two hours. After cooling, the sodium bromide which has precipitated is filtered off, and the filtrate is concentrated in a water-jet vacuum. The residue is taken up in 400 ml of ether and 200 ml of water. The organic phase is separated in a separating funnel from the aqueous phase, washed repeatedly with water, dried over sodium sulphate and concentrated in a water-jet vacuum to leave as residue 1-[(naphtho[1,2-b]thiophen-4-yl)-methyl]-1H-imidazole, m.p. 109°-111°.

Workup

  1. additionto the solution is added portionwise
  2. temperaturewith slight self-heating
  3. customhas been completely absorbed
  4. additionThere is subsequently added dropwise at the same temperature, within 60 minutes
  5. temperatureAfter cooling
  6. customthe sodium bromide which has precipitated
  7. filtrationis filtered off
  8. concentrationthe filtrate is concentrated in a water-jet vacuum
  9. customThe organic phase is separated in a separating funnel from the aqueous phase
  10. washwashed repeatedly with water
  11. dry with materialdried over sodium sulphate
  12. concentrationconcentrated in a water-jet vacuum

Sources & evidence

ORD record
ord-3f2121fdbd404d13b13c4e5cd9c92372
Source dataset
uspto-grants-1979_10
Patent number
US04171366

Reaction notes

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