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

HRID 7735

反応式

HRID 7735 の反応式
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]

参加物

6

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-6aab020e505c4013a9621c93cb7e9ea8
出典データセット
uspto-grants-2006_08
特許番号
US07087601B2

関連ノート

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