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Methyl iodide → 1-(4-Bromobenzyl)-3-methylimidazolidine-2,4-dione

HRID 1891255
ノート
印刷プレビュー

反応式

HRID 1891255 の反応式
[Br:1][C:2]1[CH:15]=[CH:14][C:5]([CH2:6][N:7]2[CH2:11][C:10](=[O:12])[NH:9][C:8]2=[O:13])=[CH:4][CH:3]=1.[C:16](=O)([O-])[O-].[K+].[K+].IC>CN(C=O)C>[Br:1][C:2]1[CH:15]=[CH:14][C:5]([CH2:6][N:7]2[CH2:11][C:10](=[O:12])[N:9]([CH3:16])[C:8]2=[O:13])=[CH:4][CH:3]=1
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

5

反応物 3

HCID 6328Methyl iodide2 回HCID 11430Potassium CarbonateHCID 154067221-(4-Bromobenzyl)imidazolidine-2,4-dione

生成物 1

HCID 668132201-(4-Bromobenzyl)-3-methylimidazolidine-2,4-dione収率 83.2%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
50 °C

実験手順

1-(4-Bromobenzyl)imidazolidine-2,4-dione (1B4) (1.86 mmol, 500 mg) was dissolved in DMF (7 ml) and potassium carbonate (5.57 mmol, 770 mg) and iodomethane (1B5) (1.86 mmol, 0.116 ml, 264 mg) were added and the reaction mixture was stirred at 50° C. under nitrogen. The reaction was monitored by TLC and after 48 h of heating some starting material remained. An additional 2 equivalents of iodomethane (3.72 mmol, 0.232 ml, 528 mg) was added and the mixture stirred at 75° C. under nitrogen overnight. The reaction mixture was cooled to room temperature, filtrated and concentrated, then purified on silica eluting with heptane/EtOAc/EtOH 5/4/1 to give 1-(4-bromobenzyl)-3-methylimidazolidine-2,4-dione (1B6) 438 mg, (83%); 1H NMR (400 MHz, CDCl3) 7.51 (d, 2H) 7.15 (d, 2H) 4.53 (s, 2H) 3.74 (s, 2H) 3.06 (s, 3H).

後処理

  1. temperatureof heating some starting material
  2. stirringthe mixture stirred at 75° C. under nitrogen overnight
  3. temperatureThe reaction mixture was cooled to room temperature
  4. filtrationfiltrated
  5. concentrationconcentrated
  6. custompurified on silica eluting with heptane/EtOAc/EtOH 5/4/1

出典と根拠

ORDレコード
ord-846543b8db8549048b3c8374cbea17aa
出典データセット
uspto-grants-2013_08
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08507521B2

反応ノート

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