3-Hexanol → 1-Ethylbutyl N-{4-[(6,7-dimethoxy-4-quinolyl)oxy]-2,3-dimethylphenyl}carbamate

HRID 721219

反応式

HRID 721219 の反応式
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][C:12]=1[O:13][CH3:14])[N:9]=[CH:8][CH:7]=[C:6]2[O:15][C:16]1[CH:22]=[CH:21][C:19]([NH2:20])=[C:18]([CH3:23])[C:17]=1[CH3:24].Cl[C:26](Cl)([O:28]C(=O)OC(Cl)(Cl)Cl)Cl.[CH3:37][CH2:38][CH:39]([OH:43])[CH2:40][CH2:41][CH3:42].C(=O)(O)[O-].[Na+]>C(Cl)Cl.C(N(CC)CC)C.C1(C)C=CC=CC=1>[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][C:12]=1[O:13][CH3:14])[N:9]=[CH:8][CH:7]=[C:6]2[O:15][C:16]1[CH:22]=[CH:21][C:19]([NH:20][C:26](=[O:28])[O:43][CH:39]([CH2:38][CH3:37])[CH2:40][CH2:41][CH3:42])=[C:18]([CH3:23])[C:17]=1[CH3:24]

参加物

8

反応物 4

HCID 121783-HexanolHCID 94429TriphosgeneHCID 516892Sodium BicarbonateHCID 218904394-[(6,7-Dimethoxy-4-quinolyl)oxy]-2,3-dimethylaniline

生成物 1

HCID 218909421-Ethylbutyl N-{4-[(6,7-dimethoxy-4-quinolyl)oxy]-2,3-dimethylphenyl}carbamate収率 55.9%

試薬・触媒・溶媒 3

HCID 1140Toluene溶媒HCID 6344Dichloromethane溶媒HCID 8471Triethylamine溶媒

実験手順

4-[(6,7-Dimethoxy-4-quinolyl)oxy]-2,3-dimethylaniline (50 mg) was added to toluene (5 ml), and triethylamine (0.5 ml), and the mixture was heated under reflux to prepare a solution. A solution of triphosgene (68 mg) in methylene chloride was then added thereto, and the mixture was heated under reflux for 10 min. Next, 3-hexanol (24 mg) was added thereto, and the mixture was further stirred with heating under reflux for 3 hr. A saturated aqueous sodium bicarbonate solution was added to stop the reaction, and the reaction solution was then extracted with chloroform, followed by washing with a 1 N aqueous hydrochloric acid solution, water, and saturated brine in that order. The extract was dried over sodium sulfate and was then concentrated. The residue was purified on a column using chloroform/methanol to give the title compound (39 mg, yield 53%).

後処理

  1. temperaturethe mixture was heated
  2. temperatureunder reflux
  3. customto prepare a solution
  4. temperaturethe mixture was heated
  5. temperatureunder reflux for 10 min
  6. temperaturewith heating
  7. temperatureunder reflux for 3 hr
  8. customthe reaction
  9. extractionthe reaction solution was then extracted with chloroform
  10. washby washing with a 1 N aqueous hydrochloric acid solution, water, and saturated brine in that order
  11. dry with materialThe extract was dried over sodium sulfate
  12. concentrationwas then concentrated
  13. customThe residue was purified on a column

出典と根拠

ORDレコード
ord-d8d6ef0f262642c29ea73b780ef98cc4
出典データセット
uspto-grants-2006_11
特許番号
US07135466B2

関連ノート

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