2-Aminophenol → 3,5-dimethoxy-N-(2-methoxyphenyl)-4-methylbenzamide

HRID 7735

반응식

HRID 7735 반응식
S(Cl)(Cl)=O.[CH3:5][O:6][C:7]1[CH:8]=[C:9]([CH:13]=[C:14]([O:17][CH3:18])[C:15]=1[CH3:16])[C:10]([OH:12])=O.[NH2:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=1[OH:26].[CH:27](N(C(C)C)CC)(C)C>C1COCC1>[CH3:18][O:17][C:14]1[CH:13]=[C:9]([CH:8]=[C:7]([O:6][CH3:5])[C:15]=1[CH3:16])[C:10]([NH:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=1[O:26][CH3:27])=[O:12]

참가 물질

6

반응물 4

HCID 58012-AminophenolHCID 24386Thionyl ChlorideHCID 81531DiisopropylethylamineHCID 37644863,5-Dimethoxy-4-methylbenzoic acid

생성물 1

HCID 25993393,5-dimethoxy-N-(2-methoxyphenyl)-4-methylbenzamide

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

Thionyl chloride (10 mL) and 3,5-dimethoxy-4-methylbenzoic acid (1.0 g, 5.1 mmol) was refluxed under argon until no starting material was observed by TLC. After cooling reaction mixture to rt, concentrated mixture in vacuo. The resulting brown oil was added to a mixture of 2-aminophenol (580 mg, 5.3 mmol), diisopropylethyl amine (1.1 mL, 6.3 mmol) and THF (40 mL) at 0° C. and then brought to rt overnight. After concentrating mixture in vacuo, the resulting brown oil was purified by flash chromatography on silica gel, using a gradient elution from 1:9 EtOAc:hexanes to 1:1 EtOAc:hexanes. This afforded the desired intermediate, 3,5-dimethoxy-N-(2-methoxyphenyl)-4-methylbenzamide, as a colorless solid.

후처리

  1. temperatureAfter cooling
  2. customreaction mixture to rt
  3. concentrationconcentrated mixture in vacuo
  4. concentrationAfter concentrating mixture in vacuo
  5. customthe resulting brown oil was purified by flash chromatography on silica gel
  6. washa gradient elution from 1:9 EtOAc

출처 및 근거

ORD 기록
ord-6aab020e505c4013a9621c93cb7e9ea8
출처 데이터셋
uspto-grants-2006_08
특허 번호
US07087601B2

연결된 노트

불러오는 중…