Water → 5-[[3,5-Bis(1,1-dimethylethyl)-4-hydroxyphenyl]methylene]-2-thioxo-4-imidazolidinone

HRID 486104

반응식

HRID 486104 반응식
[C:1]([C:5]1[CH:6]=[C:7]([CH:10]=[C:11]([C:14]([CH3:17])([CH3:16])[CH3:15])[C:12]=1[OH:13])[CH:8]=O)([CH3:4])([CH3:3])[CH3:2].[NH:18]1[CH2:24][C:22](=[O:23])[NH:21][C:19]1=[S:20].C([O-])(=O)C.[Na+].O>C(O)(=O)C>[CH3:4][C:1]([C:5]1[CH:6]=[C:7]([CH:8]=[C:24]2[NH:18][C:19](=[S:20])[NH:21][C:22]2=[O:23])[CH:10]=[C:11]([C:14]([CH3:17])([CH3:16])[CH3:15])[C:12]=1[OH:13])([CH3:2])[CH3:3]

참가 물질

6

반응물 4

HCID 962WaterHCID 732193,5-Di-tert-butyl-4-hydroxybenzaldehydeHCID 517045Sodium AcetateHCID 12740302-Thiohydantoin

생성물 1

HCID 541342535-[[3,5-Bis(1,1-dimethylethyl)-4-hydroxyphenyl]methylene]-2-thioxo-4-imidazolidinone수율 57.8%

시약·촉매·용매 1

HCID 176Acetic Acid용매

실험 절차

A mixture of 3,5-di-tert-butyl-4-hydroxybenzaldehyde (30.0 g, 128 mmols), 2-thiohydantoin (14.8 g, 128 mmols), and sodium acetate (36 g) in acetic acid (200 ml) is stirred under nitrogen and heated to reflux. After 24 hours the mixture is allowed to cool, and is stirred into water (2 L). After an hour the product is filtered off, washed three times with water, and dried. Recrystallization from acetonitrile gave the 5-[[3,5-bis(1,1-dimethylethyl)-4-hydroxyphenyl]methylene]-2-thioxo-4-imidazolidinone (24.6 g), mp 278°-279° C. (dec).

후처리

  1. temperatureheated to reflux
  2. temperatureto cool
  3. filtrationAfter an hour the product is filtered off
  4. washwashed three times with water
  5. customdried
  6. customRecrystallization from acetonitrile

출처 및 근거

ORD 기록
ord-a59b2f68367049babe8d084d0602202c
출처 데이터셋
uspto-grants-1994_03
특허 번호
US05290800

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