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

HRID 5897

반응식

HRID 5897 반응식
[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

참가 물질

6

반응물 3

HCID 313Hydrochloric Acid2회HCID 978575-BenzylidenehydantoinHCID 542510915-[[3-Methoxy-2-(phenylmethoxy)phenyl]methylene]-2,4-imidazolidinedione

생성물 1

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

시약·촉매·용매 2

HCID 23994Zinc촉매HCID 887Methanol용매

반응 조건

온도
50 °C

실험 절차

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. Recrystallization from methanol gives pure product; mp 205°-207° C.

후처리

  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

출처 및 근거

ORD 기록
ord-3b6e898593fa40f990872efa8f46e0d5
출처 데이터셋
uspto-grants-1993_09
특허 번호
US05246943

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