5-Methoxy-1-benzothiophene → 7-(5-methoxybenzo[b]thiophen-2-yl)-6,7-dihydro-5H-pyrrolo[1,2-c]imidazol-7-ol

HRID 724219Notes

Reaction equation

HRID 724219 reaction equation
[CH3:1][O:2][C:3]1[CH:11]=[CH:10][C:6]2[S:7][CH:8]=[CH:9][C:5]=2[CH:4]=1.CCCCCC.C([Li])CCC.[CH:23]1[N:27]=[CH:26][N:25]2[CH2:28][CH2:29][C:30](=[O:31])[C:24]=12>C1COCC1.[Cl-].[Na+].O>[CH3:1][O:2][C:3]1[CH:11]=[CH:10][C:6]2[S:7][C:8]([C:30]3([OH:31])[C:24]4[N:25]([CH:26]=[N:27][CH:23]=4)[CH2:28][CH2:29]3)=[CH:9][C:5]=2[CH:4]=1

Participants

6

Reactant 3

HCID 36324255-Methoxy-1-benzothiopheneHCID 111709605,6-Dihydropyrrolo[1,2-c]imidazol-7-oneHCID 178418244HCID 178418244, compound

Product 1

HCID 99656767-(5-methoxybenzo[b]thiophen-2-yl)-6,7-dihydro-5H-pyrrolo[1,2-c]imidazol-7-olYield 56.9%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 57417360Sodium chloride; waterSolvent

Procedure

A solution of 5-methoxybenzo[b]thiophene (0.33 g) in THF (8 ml) was cooled to −78° C., and an n-butyl lithium hexane solution (1.6 M; 1.4 ml) was added dropwise to this solution. The mixture was stirred for 1 h at the same temperature, and a solution of 5,6-dihydro-7H-pyrrolo[1,2-c]imidazol-7-one (0.18 g) in THF (3 ml) was added to this solution. The reaction mixture was stirred for 1 h at the same temperature, and saturated brine was added. The mixture was warmed to room temperature and the organic layer was separated. The organic layer was diluted with ethyl acetate, washed with saturated brine and dried over anhydrous magnesium sulfate. The solvent was evaporated. The residue was suspended in ethyl acetate and filtrated to give the title compound (0.24 g) as pale brown crystals. The crystals were recrystallized from THF to give the title compound (0.13 g) as colorless crystals.

Workup

  1. additionwas added
  2. customthe organic layer was separated
  3. additionThe organic layer was diluted with ethyl acetate
  4. washwashed with saturated brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customThe solvent was evaporated
  7. filtrationfiltrated

Sources & evidence

ORD record
ord-76a366ba373748298458c4780b7395f4
Source dataset
uspto-grants-2006_11
Patent number
US07141598B2

Reaction notes

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