Water → HCID 19860555, compound

HRID 2072796Notes

Reaction equation

HRID 2072796 reaction equation
[CH3:1][C:2]1[N:3]=[CH:4][NH:5][CH:6]=1.[H-].[Na+].[CH3:9][O:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=1[C:17]1[S:18][CH:19]=[C:20]([CH2:22]Cl)[N:21]=1.O>O1CCCC1>[CH3:9][O:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=1[C:17]1[S:18][CH:19]=[C:20]([CH2:22][N:3]2[C:2]([CH3:1])=[CH:6][N:5]=[CH:4]2)[N:21]=1

Participants

6

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 2110925HCID 2110925, compoundHCID 178418800HCID 178418800, compound

Product 1

HCID 19860555HCID 19860555, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
5 °C

Procedure

To a solution of 82 mg of 4-methylimidazole in 10 ml of tetrahydrofuran at 5° C. was added 50 mg of sodium hydride in 50% oil and the resulting mixture stirred at 5° C. for 20 minutes. 2-(o-Methoxyphenyl)-4-chloromethylthiazole (240 mg) in 5 ml of the same solvent was added and the reation mixture heated at reflux for 2 hours. The reaction mixture was cooled to room temperature and treated with 1 ml of water. The water and solvent were removed in vacuo and the residue dissolved in chloroform. The chloroform solution was washed with a brine solution, dried over sodium sulfate and concentrated to give 250 mg of crude product. The product was obtained by chromatography on 7 g of silica gel (chloroform-methanol), 40:1-v:v), 100 mg.

Workup

  1. temperaturethe reation mixture heated
  2. temperatureat reflux for 2 hours
  3. temperatureThe reaction mixture was cooled to room temperature
  4. customThe water and solvent were removed in vacuo
  5. dissolutionthe residue dissolved in chloroform
  6. washThe chloroform solution was washed with a brine solution
  7. dry with materialdried over sodium sulfate
  8. concentrationconcentrated
  9. customto give 250 mg of crude product
  10. customThe product was obtained by chromatography on 7 g of silica gel (chloroform-methanol), 40

Sources & evidence

ORD record
ord-ba226cb262d54e6da36641c9459faac8
Source dataset
uspto-grants-1990_04
Patent number
US04914207

Reaction notes

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