N-Methylol-alpha-chloroacetamide → 2-Acetyl-4-tert-butyl-6-(N-chloroacetylaminomethyl)phenol

HRID 1389562노트

반응식

HRID 1389562 반응식
[C:1]([C:4]1[CH:9]=[C:8]([C:10]([CH3:13])([CH3:12])[CH3:11])[CH:7]=[CH:6][C:5]=1[OH:14])(=[O:3])[CH3:2].O[CH2:16][NH:17][C:18](=[O:21])[CH2:19][Cl:20]>C(O)(=O)C.S(=O)(=O)(O)O>[C:1]([C:4]1[CH:9]=[C:8]([C:10]([CH3:13])([CH3:12])[CH3:11])[CH:7]=[C:6]([CH2:16][NH:17][C:18](=[O:21])[CH2:19][Cl:20])[C:5]=1[OH:14])(=[O:3])[CH3:2]

참가 물질

5

반응물 2

HCID 62466N-Methylol-alpha-chloroacetamideHCID 2630921-(5-Tert-butyl-2-hydroxyphenyl)ethan-1-one

생성물 1

HCID 202969572-Acetyl-4-tert-butyl-6-(N-chloroacetylaminomethyl)phenol수율 85.9%

시약·촉매·용매 2

HCID 176Acetic Acid용매HCID 1118Sulfuric Acid용매

반응 조건

온도
60 °C

실험 절차

To 2.88 g of 2-acetyl-4-tert-butylphenol (prepared in Reference Example 2) dissolved in 20 ml of a mixed solution of glacial acetic acid and conc. sulfuric acid (10:1) were added 2.78 g of N-hydroxymethylchloroacetamide at room temperature and stirred at 60° C. for 2 hours. The reaction mixture was poured into 100 ml of ice-water, extracted with diethyl ether and the extract was washed with water and saturated brine successively, dried over magnesium sulfate anhydride and concentrated at reduced pressure. The residue was chromatographed on silica gel column using a mixed solvent of methylene chloride and ethyl acetate (50:1) as an eluting agent to give 3.83 g of the title compound having the following physical properties.

후처리

  1. extractionextracted with diethyl ether
  2. washthe extract was washed with water and saturated brine successively
  3. dry with materialdried over magnesium sulfate anhydride
  4. concentrationconcentrated at reduced pressure
  5. customThe residue was chromatographed on silica gel column

출처 및 근거

ORD 기록
ord-b650a8b2c1334530970227c7fc82ac9e
출처 데이터셋
uspto-grants-1981_01
특허 번호
US04245099

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