Potassium Iodide → Ethyl 4-[N-(3-cyano-4-neopentyloxyphenyl)carbamoyl]-3-methylpyrazol-1-ylacetate

HRID 1744579Notes

Reaction equation

HRID 1744579 reaction equation
[C:1]([C:3]1[CH:4]=[C:5]([NH:15][C:16]([C:18]2[CH:19]=[N:20][NH:21][C:22]=2[CH3:23])=[O:17])[CH:6]=[CH:7][C:8]=1[O:9][CH2:10][C:11]([CH3:14])([CH3:13])[CH3:12])#[N:2].C(=O)([O-])[O-].[K+].[K+].[I-].[K+].Br[CH2:33][C:34]([O:36][CH2:37][CH3:38])=[O:35]>O.C1(C)C=CC=CC=1.CN(C)C=O>[C:1]([C:3]1[CH:4]=[C:5]([NH:15][C:16]([C:18]2[C:22]([CH3:23])=[N:21][N:20]([CH2:33][C:34]([O:36][CH2:37][CH3:38])=[O:35])[CH:19]=2)=[O:17])[CH:6]=[CH:7][C:8]=1[O:9][CH2:10][C:11]([CH3:14])([CH3:13])[CH3:12])#[N:2]

Participants

8

Reactant 4

HCID 4875Potassium IodideHCID 7748Ethyl bromoacetateHCID 11430Potassium CarbonateHCID 22227878N-(3-Cyano-4-neopentyloxyphenyl)-5-methylpyrazole-4-carboxamide

Product 1

HCID 22228013Ethyl 4-[N-(3-cyano-4-neopentyloxyphenyl)carbamoyl]-3-methylpyrazol-1-ylacetateYield 22.9%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 1140TolueneSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

N-(3-Cyano-4-neopentyloxyphenyl)-5-methylpyrazole-4-carboxamide (2.4 g), potassium carbonate (1.1 g), potassium iodide (1.4 g) and ethyl bromoacetate (1.4 g) were added to a mixed solvent of dimethylformamide (24 ml) and toluene (24 ml) and the mixture was stirred at 60° C. for 4 h. The reaction mixture was added into water, washed with dilute hydrochloric acid and saturated brine, and dried over anhydrous magnesium sulfate, after which the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (mobile phase: chloroform). Methylene chloride was added to the obtained oily substance to allow crystallization. The crystals were recrystallized from a mixed solvent of methylene chloride-n-hexane to give the title compound (0.7 g), melting point: 240° C.

Workup

  1. washwashed with dilute hydrochloric acid and saturated brine
  2. dry with materialdried over anhydrous magnesium sulfate
  3. customafter which the solvent was evaporated under reduced pressure
  4. customThe residue was purified by silica gel column chromatography (mobile phase: chloroform)
  5. additionMethylene chloride was added to the obtained oily substance
  6. customcrystallization
  7. customThe crystals were recrystallized from a mixed solvent of methylene chloride-n-hexane

Sources & evidence

ORD record
ord-8e84ce2ce74b432aa0657e6324214d87
Source dataset
uspto-grants-2006_03
Patent number
US07015218B1

Reaction notes

Loading…