Methanol → HCID 178493972, compound

HRID 1720289Notes

Reaction equation

HRID 1720289 reaction equation
[CH3:1][OH:2].C[O-].[Na+].C(S([C:11]1[N:20]([CH2:21][C:22]2[CH:27]=[CH:26][C:25]([C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][C:29]=3[C:34]3[NH:38][N:37]=[N:36][N:35]=3)=[CH:24][CH:23]=2)[C:14]2=[N:15][CH:16]=[CH:17][C:18]([CH3:19])=[C:13]2[N:12]=1)(=O)=O)C>ClCCl>[CH3:1][O:2][C:11]1[N:20]([CH2:21][C:22]2[CH:27]=[CH:26][C:25]([C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][C:29]=3[C:34]3[NH:38][N:37]=[N:36][N:35]=3)=[CH:24][CH:23]=2)[C:14]2=[N:15][CH:16]=[CH:17][C:18]([CH3:19])=[C:13]2[N:12]=1

Participants

5

Reactant 3

HCID 887Methanol2×HCID 10942334Sodium MethoxideHCID 178477664HCID 178477664, compound

Product 1

HCID 178493972HCID 178493972, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

420 mg (2.2 mmol) of 28% methanol solution of sodium methoxide was added to 10 ml of a methanol solution of 0.44 g (0.96 mmol) of 2-ethylsulfonyl-7-methyl-3[(2'-(1H-tetrazol-5-yl)biphenyl-4-yl)methyl]- 3H-imidazo[4.5-b]-pyridine was dispersed in 150 ml of dichloromethane. The mixture was refluxed for 40 minutes. The solvent was distilled out at a reduced pressure. The residue was mixed with water and neutralized with 2N HCl. An extract with dichloromethane was washed with a saturated saline and dried with anhydrous magnesium sulfate. The solvent was distilled out at a reduced pressure. The residue was treated with ethanol and ether for recrystallization to obtain 300 mg of the above named compound.

Workup

  1. temperatureThe mixture was refluxed for 40 minutes
  2. distillationThe solvent was distilled out at a reduced pressure
  3. additionThe residue was mixed with water and neutralized with 2N HCl
  4. extractionAn extract with dichloromethane
  5. washwas washed with a saturated saline
  6. dry with materialdried with anhydrous magnesium sulfate
  7. distillationThe solvent was distilled out at a reduced pressure
  8. additionThe residue was treated with ethanol and ether for recrystallization
  9. customto obtain 300 mg of the

Sources & evidence

ORD record
ord-dbc0b5a915f74d0dbecee353ba585f7f
Source dataset
uspto-grants-1996_04
Patent number
US05506238

Reaction notes

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