p-Toluenesulfonic acid monohydrate → 2-(3,5-Dimethoxy-4-methylphenyl)-1,3-benzoxazole

HRID 7736

反応式

HRID 7736 の反応式
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:17]=[C:18]([O:21][CH3:22])[C:19]=1[CH3:20])[C:6]([NH:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[O:15]C)=O.O.C1(C)C=CC(S(O)(=O)=O)=CC=1>C1(C)C=CC=CC=1>[CH3:22][O:21][C:18]1[CH:17]=[C:5]([C:6]2[O:15][C:10]3[CH:11]=[CH:12][CH:13]=[CH:14][C:9]=3[N:8]=2)[CH:4]=[C:3]([O:2][CH3:1])[C:19]=1[CH3:20]

参加物

4

反応物 2

HCID 521998p-Toluenesulfonic acid monohydrateHCID 25993393,5-dimethoxy-N-(2-methoxyphenyl)-4-methylbenzamide

生成物 1

HCID 219909742-(3,5-Dimethoxy-4-methylphenyl)-1,3-benzoxazole

試薬・触媒・溶媒 1

HCID 1140Toluene溶媒

実験手順

A mixture of 3,5-dimethoxy-N-(2-methoxyphenyl)-4-methylbenzamide (1.29 g, 4.49 mmol), toluene (22 mL), p-toluenesulfonic acid monohydrate (5.9 g, 31 mmol) and molecular sieves was refluxed until no starting material was observed by TLC. Cooled mixture to rt and filtered, washing with warm chloroform. Removal of solvent from filtrate afforded a yellow solid. Purification of crude solid by flash chromatography on silica gel using 1:3 EtOAc:hexanes gave the desired intermediate, 2-(3,5-dimethoxy-4-methylphenyl)-1,3-benzoxazole, as a colorless solid.

後処理

  1. temperaturewas refluxed until no starting material
  2. filtrationfiltered
  3. washwashing with warm chloroform
  4. customRemoval of solvent from filtrate
  5. customafforded a yellow solid
  6. customPurification of crude solid by flash chromatography on silica gel using 1:3 EtOAc

出典と根拠

ORDレコード
ord-450eaf900c1b41f5a2503bdf4b4d4c54
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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