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

HRID 1744579ノート

反応式

HRID 1744579 の反応式
[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]

参加物

8

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 3

HCID 962Water溶媒HCID 1140Toluene溶媒HCID 6228Dimethylformamide溶媒

反応条件

温度
60 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-8e84ce2ce74b432aa0657e6324214d87
出典データセット
uspto-grants-2006_03
特許番号
US07015218B1

反応ノート

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