Dimethylformamide → HCID 136368367, compound

HRID 502989Notes

Reaction equation

HRID 502989 reaction equation
C([S-])C.[Na+].CN(C=O)C.[Cl:10][C:11]1[CH:16]=[C:15]([O:17]C)[CH:14]=[CH:13][C:12]=1[C:19]1[N:23]([CH3:24])[C:22]([C:25]2([C:30]3[S:31][CH:32]=[CH:33][CH:34]=3)[CH2:29][CH2:28][CH2:27][CH2:26]2)=[N:21][N:20]=1>C(Cl)(Cl)Cl>[Cl:10][C:11]1[CH:16]=[C:15]([OH:17])[CH:14]=[CH:13][C:12]=1[C:19]1[N:23]([CH3:24])[C:22]([C:25]2([C:30]3[S:31][CH:32]=[CH:33][CH:34]=3)[CH2:29][CH2:28][CH2:27][CH2:26]2)=[N:21][N:20]=1

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 4459711Sodium ethanethiolateHCID 68468817HCID 68468817, compound

Product 1

HCID 136368367HCID 136368367, compoundYield 10.4%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Conditions

Temperature
100 °C

Procedure

Sodium ethanethiolate was added to a DMF (10 ml) solution of 3-(2-chloro-4-methoxyphenyl)-4-methyl-5-[1-(2-thienyl)cyclopentyl]-4H-1,2,4-triazole (300 mg), followed by stirring at 100° C. for 2 hours. After the reaction solution and chloroform were added to distilled water, the organic layer was separated. Furthermore, the organic layer washed with a saturated sodium chloride solution, dried over anhydrous magnesium sulfate, and filtered and then the solvent was removed by evaporation under reduced pressure. The resulting crude product was purified by flash column chromatography (chloroform:methanol=97:3) and then the resulting solid was recrystallized from isopropanol to obtain 30 mg of 3-chloro-4-{4-methyl-5-[1-(2-thienyl)cyclopentyl]-4H-1,2,4-triazol-3-yl}phenol (colorless solid).

Workup

  1. distillationto distilled water
  2. customthe organic layer was separated
  3. washFurthermore, the organic layer washed with a saturated sodium chloride solution
  4. dry with materialdried over anhydrous magnesium sulfate
  5. filtrationfiltered
  6. customthe solvent was removed by evaporation under reduced pressure
  7. customThe resulting crude product was purified by flash column chromatography (chloroform:methanol=97:3)
  8. customthe resulting solid was recrystallized from isopropanol

Sources & evidence

ORD record
ord-d75a0c3cbdf54a5aa985e4b79512b1ed
Source dataset
uspto-grants-2010_08
Patent number
US07776897B2

Reaction notes

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