Sodium Hydroxide → HCID 13913564, compound

HRID 330021Notes

Reaction equation

HRID 330021 reaction equation
[OH-].[Na+].[CH3:3][O:4][C:5]1[CH:6]=[C:7]([CH:15]([S:22][C:23]2[CH:32]=[CH:31][C:26]([C:27]([O:29]C)=[O:28])=[CH:25][CH:24]=2)[CH2:16][N:17]2[CH:21]=[CH:20][N:19]=[CH:18]2)[CH:8]=[C:9]([O:13][CH3:14])[C:10]=1[O:11][CH3:12]>CO>[CH3:3][O:4][C:5]1[CH:6]=[C:7]([CH:15]([S:22][C:23]2[CH:24]=[CH:25][C:26]([C:27]([OH:29])=[O:28])=[CH:31][CH:32]=2)[CH2:16][N:17]2[CH:21]=[CH:20][N:19]=[CH:18]2)[CH:8]=[C:9]([O:13][CH3:14])[C:10]=1[O:11][CH3:12]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 19870526HCID 19870526, compound

Product 1

HCID 13913564HCID 13913564, compoundYield 55.4%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

1.6 ml of a 1N aqueous solution of sodium hydroxide was added to a solution of 170.6 mg of methyl 4-[1-(3,4,5-trimethoxyphenyl)-2-(imidazol-1-yl)ethylthio]benzoate (prepared as described in Example 27) in 1.6 ml of methanol, and the reaction mixture was stirred at room temperature for 2 hours. The solvent was then removed by distillation under reduced pressure, and 0.8 ml of a 1N aqueous solution of sodium hydroxide was added to the residue. The resulting mixture was extracted with chloroform, and the aqueous layer was adjusted to a pH value of 6.0 using concentrated hydrochloric acid and then extracted with chloroform. The chloroform extract was washed with a concentrated aqueous solution of sodium chloride and dried. The solvent was removed by distillation under reduced pressure, to give 91.4 mg of the title compound as a powdery substance, melting at 94°-97° C.

Workup

  1. customThe solvent was then removed by distillation under reduced pressure, and 0.8 ml of a 1N aqueous solution of sodium hydroxide
  2. additionwas added to the residue
  3. extractionThe resulting mixture was extracted with chloroform
  4. extractionextracted with chloroform
  5. extractionThe chloroform extract
  6. washwas washed with a concentrated aqueous solution of sodium chloride
  7. customdried
  8. customThe solvent was removed by distillation under reduced pressure

Sources & evidence

ORD record
ord-d2e526a31250484fb9552daa9b54c212
Source dataset
uspto-grants-1990_01
Patent number
US04894385

Reaction notes

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