Hydrochloric Acid → (RS)-5-[[3-Methoxy-2-(phenylmethoxy)phenyl]methyl]-2,4-imidazolidinedione

HRID 260074

反応式

HRID 260074 の反応式
[CH3:1][O:2][C:3]1[C:4]([O:17][CH2:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)=[C:5]([CH:9]=[C:10]2[NH:14][C:13](=[O:15])[NH:12][C:11]2=[O:16])[CH:6]=[CH:7][CH:8]=1.Cl.C(=C1NC(=O)NC1=O)C1C=CC=CC=1>CO.[Zn]>[CH3:1][O:2][C:3]1[C:4]([O:17][CH2:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)=[C:5]([CH2:9][CH:10]2[NH:14][C:13](=[O:15])[NH:12][C:11]2=[O:16])[CH:6]=[CH:7][CH:8]=1

参加物

6

反応物 3

HCID 313Hydrochloric Acid2 回HCID 978575-BenzylidenehydantoinHCID 542510915-[[3-Methoxy-2-(phenylmethoxy)phenyl]methylene]-2,4-imidazolidinedione

生成物 1

HCID 15296728(RS)-5-[[3-Methoxy-2-(phenylmethoxy)phenyl]methyl]-2,4-imidazolidinedione収率 47.1%

試薬・触媒・溶媒 2

HCID 23994Zinc触媒HCID 887Methanol溶媒

反応条件

温度
50 °C

実験手順

Zinc powder (40.00 g; 0.61 mole) is added to a stirred suspension of 48.00 g (0.16 mole) of the benzylidine hydantoin from Example 3 in 1,200 mL of methanol under nitrogen. Concentrated hydrochloric acid (30 mL) is added and the mixture is heated on the steam bath for 20 minutes (after 10 minutes the starting benzylidene hydantoin dissolves). Another 30 mL of concentrated hydrochloric acid is added and the mixture is heated at reflux for another 20 minutes. The cooled (50° C.) mixture is cautiously filtered and the cake washed with 100 mL of methanol. Water (500 mL) is added to the filtrate to yield 24.60 g of crystalline product; mp 202°-204° C.

後処理

  1. dissolutiondissolves)
  2. temperaturethe mixture is heated
  3. temperatureat reflux for another 20 minutes
  4. filtrationis cautiously filtered
  5. washthe cake washed with 100 mL of methanol
  6. additionWater (500 mL) is added to the filtrate

出典と根拠

ORDレコード
ord-edf479c62b5844d892dc201bc6071dd9
出典データセット
uspto-grants-1996_06
特許番号
US05525614

関連ノート

読み込み中…