Iodoethane → HCID 19879226, compound

HRID 1885586Notes

Reaction equation

HRID 1885586 reaction equation
Br.Br.[OH:3][C:4]1[CH:9]=[CH:8][C:7]([C:10]2[N:11]=[C:12]3[CH2:23][CH2:22][CH2:21][N:13]3[C:14]=2[C:15]2[CH:20]=[CH:19][N:18]=[CH:17][CH:16]=2)=[CH:6][CH:5]=1.[H-].[Na+].[CH2:26](I)[CH3:27]>CN(C)C=O>[CH2:26]([O:3][C:4]1[CH:5]=[CH:6][C:7]([C:10]2[N:11]=[C:12]3[CH2:23][CH2:22][CH2:21][N:13]3[C:14]=2[C:15]2[CH:20]=[CH:19][N:18]=[CH:17][CH:16]=2)=[CH:8][CH:9]=1)[CH3:27]

Participants

5

Reactant 3

HCID 6340Iodoethane2×HCID 24758Sodium hydride2×HCID 136403394HCID 136403394, compound

Product 1

HCID 19879226HCID 19879226, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

A stirred solution of 1.2 g (2.7 mmoles) of 2-(4-hydroxyphenyl)-3-(4-pyridyl)-6,7-dihydro-[5H]-pyrrolo-[1,2-a]imidazole dihydrobromide of Example 10 in 25 ml of dry dimethylformamide cooled in an ice bath was treated with 360 mg (9.0 mmoles) of 60% sodium hydride dispersion and allowed to warm to room temperature. A solution of 420 mg (2.7 mmoles) of ethyl iodide in 2 ml of dimethylformamide was added dropwise, and after 2 hours an additional 105 mg (0.67 mmole) of ethyl iodide was added followed by another 90 mg (2.25 mmoles) of 60% sodium hydride suspension. After stirring overnight, the mixture was poured into 10 volumes of ice water and extracted three times with ethyl acetate. The organic phase was washed with water, dried over anhydrous potassium carbonate and concentrated in vacuo. The residue was flash chromatographed on silica and the fractions eluting with 4 to 6% methanol in chloroform were combined, concentrated in vacuo, and recrystallized from ethyl acetate to afford the titled compound, mp 133°-135° C. Anal. Calcd. for C19H19N3O: C, 74.73, H, 6.27; N, 13.76. Found: C, 74.23; H, 6.01; N, 13.74.

Workup

  1. extractionextracted three times with ethyl acetate
  2. washThe organic phase was washed with water
  3. dry with materialdried over anhydrous potassium carbonate
  4. concentrationconcentrated in vacuo
  5. customchromatographed on silica
  6. washthe fractions eluting with 4 to 6% methanol in chloroform
  7. concentrationconcentrated in vacuo
  8. customrecrystallized from ethyl acetate

Sources & evidence

ORD record
ord-52bc4a22dc514f2ebf57b77378f8664c
Source dataset
uspto-grants-1992_09
Patent number
US05145858

Reaction notes

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