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Triphosgene → 1-(3-Fluorophenyl)ethyl N-{4-[(6,7-dimethoxy-4-quinolyl)oxy]-2,5-dimethylphenyl}carbamate

HRID 721057
ノート
印刷プレビュー

反応式

HRID 721057 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[C:22]([CH3:23])=[CH:21][C:19]([NH2:20])=[C:18]([CH3:24])[CH:17]=1.C1(C)C=CC=CC=1.C(N(CC)CC)C.Cl[C:40](Cl)([O:42]C(=O)OC(Cl)(Cl)Cl)Cl.[F:51][C:52]1[CH:53]=[C:54]([CH:58]=[CH:59][CH:60]=1)[CH:55]([OH:57])[CH3:56]>C(Cl)Cl>[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[C:22]([CH3:23])=[CH:21][C:19]([NH:20][C:40](=[O:42])[O:57][CH:55]([C:54]2[CH:58]=[CH:59][CH:60]=[C:52]([F:51])[CH:53]=2)[CH3:56])=[C:18]([CH3:24])[CH:17]=1
参加物実験手順後処理出典と根拠反応ノート

参加物

6

反応物 4

HCID 94429TriphosgeneHCID 953483-Fluoro-alpha-methylbenzenemethanolHCID 218904214-((6,7-Dimethoxyquinolin-4-yl)oxy)-2,5-dimethylanilineHCID 22504574Toluene triethylamine

生成物 1

HCID 218908311-(3-Fluorophenyl)ethyl N-{4-[(6,7-dimethoxy-4-quinolyl)oxy]-2,5-dimethylphenyl}carbamate収率 73.6%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

4-[(6,7-Dimethoxy-4-quinolyl)oxy]-2,5-dimethylaniline (97 mg) was added to toluene/triethylamine=10/1 (10 ml), and the mixture was heated under reflux to prepare a solution. A solution of triphosgene (150 mg) in methylene chloride was then added to the solution, and the mixture was heated under reflux for 15 min. Subsequently, 3-fluoro-α-methylbenzyl alcohol (70 mg) was added thereto, and the mixture was further stirred with heating under reflux for 2 hr. After the completion of the reaction, the reaction solution was allowed to cool to room temperature before distilled water was added thereto. The mixture was subjected to separatory extraction with chloroform, followed by washing with a 1 N aqueous hydrochloric acid solution and saturated brine. The washed solution was dried over sodium sulfate and was concentrated. The residue was purified on a column using chloroform/methanol to give the title compound (108 mg, yield 68%).

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 15 min
  6. temperaturewith heating
  7. temperatureunder reflux for 2 hr
  8. customAfter the completion of the reaction
  9. distillationbefore distilled water
  10. additionwas added
  11. extractionThe mixture was subjected to separatory extraction with chloroform
  12. washby washing with a 1 N aqueous hydrochloric acid solution and saturated brine
  13. dry with materialThe washed solution was dried over sodium sulfate
  14. concentrationwas concentrated
  15. customThe residue was purified on a column

出典と根拠

ORDレコード
ord-2b1d3d3e6e814111af686b4f9bbbd370
出典データセット
uspto-grants-2006_11
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07135466B2

反応ノート

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