Potassium Hydroxide → HCID 18980957, compound

HRID 482618Notes

Reaction equation

HRID 482618 reaction equation
[F:1][C:2]([F:32])([F:31])[O:3][C:4]1[CH:9]=[CH:8][C:7]([NH:10][C:11]([N:13]2[CH2:17][CH:16]([N:18]([CH3:23])[C:19]([O:21][CH3:22])=[O:20])[C:15]([C:24]3[CH:29]=[CH:28][C:27]([OH:30])=[CH:26][CH:25]=3)=[N:14]2)=[O:12])=[CH:6][CH:5]=1.[OH-].[K+].I[CH2:36][CH2:37][CH3:38]>CS(C)=O.C(OCC)C.O>[F:32][C:2]([F:1])([F:31])[O:3][C:4]1[CH:9]=[CH:8][C:7]([NH:10][C:11]([N:13]2[CH2:17][CH:16]([N:18]([CH3:23])[C:19]([O:21][CH3:22])=[O:20])[C:15]([C:24]3[CH:29]=[CH:28][C:27]([O:30][CH2:36][CH2:37][CH3:38])=[CH:26][CH:25]=3)=[N:14]2)=[O:12])=[CH:6][CH:5]=1

Participants

7

Reactant 3

HCID 14797Potassium HydroxideHCID 336431-IodopropaneHCID 135703328HCID 135703328, compound

Product 1

HCID 18980957HCID 18980957, compound

Reagents, catalysts & solvents 3

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolventHCID 3283Diethyl EtherSolvent

Conditions

Temperature
50 °C

Procedure

To 1.0 g (2.2 mmole) of N-(4-trifluoromethoxyphenyl)-3-(4-hydroxyphenyl)-4-(N-methyl-N-(methoxycarbonyl)amino)-4,5-dihydro-1H-pyrazole-1-carboxamide (Example 297) dissolved in 7.5 ml of dimethylsulfoxide was added 0.35 g (2.8 mmole) of 45% aqueous potassium hydroxide and 1.02 g (6.0 mmole) of 1-iodopropane. The mixture was warmed to 50° C. for 30 minutes and diluted with diethyl ether and water. The organic layer was washed with brine, dried over anhydrous magnesium sulfate, filtered, concentrated in vacuo, and chromatographed over silica gel using hexane and diethyl ether to yield the title compound, a white solid, mp 153°-155° C.

Workup

  1. washThe organic layer was washed with brine
  2. dry with materialdried over anhydrous magnesium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customchromatographed over silica gel

Sources & evidence

ORD record
ord-4eae1f4aa6b74042a2dcaa7fa58a8b4d
Source dataset
uspto-grants-1998_08
Patent number
US05798311

Reaction notes

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