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

HRID 7736

반응식

HRID 7736 반응식
[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]

참가 물질

4

반응물 2

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

생성물 1

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

시약·촉매·용매 1

HCID 1140Toluene용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-450eaf900c1b41f5a2503bdf4b4d4c54
출처 데이터셋
uspto-grants-2006_08
특허 번호
US07087601B2

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