2,4,6-Trimethylphenol → 4-Chloro-2,5-dimethyl-6-(2,4,6-trimethylphenoxy)-pyrimidine

HRID 968025

反応式

HRID 968025 の反応式
[CH3:1][C:2]1[CH:7]=[C:6]([CH3:8])[CH:5]=[C:4]([CH3:9])[C:3]=1[OH:10].[H-].[Na+].[CH3:13][C:14]1[N:19]=[C:18](Cl)[C:17]([CH3:21])=[C:16]([Cl:22])[N:15]=1>C1COCC1>[Cl:22][C:16]1[C:17]([CH3:21])=[C:18]([O:10][C:3]2[C:4]([CH3:9])=[CH:5][C:6]([CH3:8])=[CH:7][C:2]=2[CH3:1])[N:19]=[C:14]([CH3:13])[N:15]=1

参加物

5

反応物 3

HCID 106982,4,6-TrimethylphenolHCID 24758Sodium hydrideHCID 2370134,6-Dichloro-2,5-dimethylpyrimidine

生成物 1

HCID 219120504-Chloro-2,5-dimethyl-6-(2,4,6-trimethylphenoxy)-pyrimidine収率 98.5%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

A solution of 2,4,6-trimethylphenol (2.720 g, 20 mmol) in 60 ml of dry THF was treated with NaH (60% in oil, 1,200 g, 30 mmol) at room temperature. After stirring at room temperature for 15 minutes, 2,5-dimethyl-4,6-dichloropyrimidine (3.34 g, 20 mmol) was added and the resulting mixture was heated at reflux for 15 hours. The mixture was quenched with saturated ammonium chloride and extracted with ethyl acetate. The organic layer was dried and concentrated to give 5.4528 g of beige solid. The solid was recrystallized from isopropanol to give 5.1345 g of pale yellow solid. mp 86-87° C.; high MS (C15H17ClN20) calc. 276.1025, found 276.10359. 1H NMR (CDCl3) δ 6.87 (s, 2H), 2.37 (s, 6H), 2.28 (s, 3H), 2.01 (s, 6H) ppm.

後処理

  1. temperaturethe resulting mixture was heated
  2. temperatureat reflux for 15 hours
  3. customThe mixture was quenched with saturated ammonium chloride
  4. extractionextracted with ethyl acetate
  5. customThe organic layer was dried
  6. concentrationconcentrated

出典と根拠

ORDレコード
ord-d04091c0d33b4d3d9d3242718af895d2
出典データセット
uspto-grants-2005_10
特許番号
US06956047B1

関連ノート

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