Imidazole → HCID 12973086, compound

HRID 2229249Notes

Reaction equation

HRID 2229249 reaction equation
[CH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[C:11]#[C:12][CH2:13]O.CS(Cl)(=O)=O.[NH:20]1[CH:24]=[CH:23][N:22]=[CH:21]1.[Na+].[I-]>C1COCC1.O.C(N(CC)CC)C>[CH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[C:11]#[C:12][CH2:13][N:20]1[CH:24]=[CH:23][N:22]=[CH:21]1

Participants

8

Reactant 4

HCID 795ImidazoleHCID 5238Sodium IodideHCID 31297Methanesulfonyl chlorideHCID 18467037HCID 18467037, compound

Product 1

HCID 12973086HCID 12973086, compoundYield 30.9%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 8028TetrahydrofuranSolventHCID 8471TriethylamineSolvent

Procedure

To a cooled (0° C.) solution of 3-(2-naphthyl)-2-propyn-1-ol (2.67 g) in THF (100 ml) were added triethylamine (4.1 ml) and methanesulfonyl chloride (1.7 ml) successively. The mixture was stirred at room temperature for 1 hours. Imidazole (3.02 g) and NaI (0.5 g) were added to the mixture and resulting mixture was stirred at 60° C. for 3 hours. To the mixture was added water, and the mixture was concentrated. The residue was extracted with ethyl acetate. The extract was washed with water and brine, dried and concentrated. The residue was chromatographed on silica gel, eluting with ethyl acetate, followed by crystallization from cyclohexane to give the titled compound (1.05 g) as a colorless solid.

Workup

  1. customresulting mixture
  2. stirringwas stirred at 60° C. for 3 hours
  3. concentrationthe mixture was concentrated
  4. extractionThe residue was extracted with ethyl acetate
  5. washThe extract was washed with water and brine
  6. customdried
  7. concentrationconcentrated
  8. customThe residue was chromatographed on silica gel
  9. washeluting with ethyl acetate
  10. customfollowed by crystallization from cyclohexane

Sources & evidence

ORD record
ord-2f9a5da2f4c14ab3911413b41edf9cea
Source dataset
uspto-grants-2002_07
Patent number
US06420375B1

Reaction notes

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