Sodium hydride → HCID 22009799, compound

HRID 322459Notes

Reaction equation

HRID 322459 reaction equation
[N:1]1([C:6]2[S:7][CH:8]=[C:9]([CH2:11][OH:12])[N:10]=2)[CH:5]=[CH:4][CH:3]=[CH:2]1.CS(Cl)(=O)=O.[H-].[Na+].O[C:21]1[CH:26]=[CH:25][C:24]([CH2:27][CH2:28][CH2:29][N:30]2[CH:34]=[CH:33][N:32]=[CH:31]2)=[CH:23][CH:22]=1>CN(C)C=O.O.C(OCC)(=O)C.C(N(CC)CC)C>[N:30]1([CH2:29][CH2:28][CH2:27][C:24]2[CH:25]=[CH:26][C:21]([O:12][CH2:11][C:9]3[N:10]=[C:6]([N:1]4[CH:2]=[CH:3][CH:4]=[CH:5]4)[S:7][CH:8]=3)=[CH:22][CH:23]=2)[CH:34]=[CH:33][N:32]=[CH:31]1

Participants

9

Reactant 4

HCID 24758Sodium hydrideHCID 31297Methanesulfonyl chlorideHCID 22009757HCID 22009757, compoundHCID 220098181-[3-(4-Hydroxyphenyl)propyl]imidazole

Product 1

HCID 22009799HCID 22009799, compoundYield 70%

Reagents, catalysts & solvents 4

HCID 962WaterSolvent2×HCID 6228DimethylformamideSolventHCID 8471TriethylamineSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a mixture of 2-(1-pyrrolyl)-4-thiazolylmethanol (0.45 g), triethylamine (0.42 ml) and ethyl acetate (20 ml) was added dripwise methanesulfonyl chloride (0.23 ml) at 0° C., and then stirred for one hour. To the reaction mixture was added water, and the ethyl acetate layer was separated, washed with water, dried (MgSO4), and concentrated under reduced pressure. The residue was dissolved in tetrahydrofuran (5 ml), which was added to a solution prepared by adding sodium hydride (oily, 60%, 92 mg) to a solution of 1-[3-(4-hydroxyphenyl)propyl]imidazole (420 mg) in N,N-dimethylformamide (10 ml). After stirring for 2 hours, the reaction mixture was poured into water and extracted with ethyl acetate. The ethyl acetate layer was washed with 2N-aqueous sodium hydroxide and then water, dried (MgSO4), and concentrated under reduced pressure. The residue was subjected to a silica gel column chromatography. From the fraction eluted with ethyl acetate-methanol (95:5, v/v), crystals were obtained. Recrystallization from ethyl acetate-hexane gave 4-[4-[3-(1-imidazolyl)propyl]phenoxymethyl]-2-(1-pyrrolyl)thiazole (530 mg, 70%), colorless prisms, mp 93-94° C.

Workup

  1. customthe ethyl acetate layer was separated
  2. washwashed with water
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated under reduced pressure
  5. dissolutionThe residue was dissolved in tetrahydrofuran (5 ml)
  6. additionwhich was added to a solution
  7. customprepared
  8. stirringAfter stirring for 2 hours
  9. extractionextracted with ethyl acetate
  10. washThe ethyl acetate layer was washed with 2N-aqueous sodium hydroxide
  11. dry with materialwater, dried (MgSO4)
  12. concentrationconcentrated under reduced pressure
  13. washFrom the fraction eluted with ethyl acetate-methanol (95:5
  14. customv/v), crystals were obtained
  15. customRecrystallization from ethyl acetate-hexane

Sources & evidence

ORD record
ord-c63d20ca04f949c980b10c7b2081cc1b
Source dataset
uspto-grants-2001_04
Patent number
US06211215B1

Reaction notes

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