Triethylamine → tert-Butyl [2-(4-fluorophenyl)-2-oxo-1-quinolin-8-ylethyl]carbamate

HRID 1170389ノート

反応式

HRID 1170389 の反応式
[N:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][C:9]=2[CH:11]([NH:22][C:23](=[O:29])[O:24][C:25]([CH3:28])([CH3:27])[CH3:26])S(C2C=CC(C)=CC=2)(=O)=O)[CH:4]=[CH:3][CH:2]=1.C(N(CC)CC)C.[F:37][C:38]1[CH:45]=[CH:44][C:41]([CH:42]=[O:43])=[CH:40][CH:39]=1.[Cl-].[NH4+]>[Br-].C([N+]1C(C)=C(CCO)SC=1)C.C(Cl)Cl.C(OCC)C>[F:37][C:38]1[CH:45]=[CH:44][C:41]([C:42](=[O:43])[CH:11]([NH:22][C:23](=[O:29])[O:24][C:25]([CH3:26])([CH3:27])[CH3:28])[C:9]2[CH:8]=[CH:7][CH:6]=[C:5]3[C:10]=2[N:1]=[CH:2][CH:3]=[CH:4]3)=[CH:40][CH:39]=1

参加物

8

反応物 4

HCID 8471TriethylamineHCID 25517Ammonium ChlorideHCID 680234-FluorobenzaldehydeHCID 86621950Tert-butyl [quinolin-8-yl(toluene-4-sulfonyl)methyl]carbamate

生成物 1

HCID 86621951tert-Butyl [2-(4-fluorophenyl)-2-oxo-1-quinolin-8-ylethyl]carbamate

試薬・触媒・溶媒 3

HCID 99649233-Ethyl-5-(2-hydroxyethyl)-4-methylthiazolium bromide触媒HCID 3283Diethyl Ether溶媒HCID 6344Dichloromethane溶媒

反応条件

温度
35 °C

実験手順

5.5 g (13 mmol) of tert-butyl [quinolin-8-yl(toluene-4-sulfonyl)methyl]carbamate, 336 mg (1.3 mmol) of 3-ethyl-5-(2-hydroxyethyl)-4-methylthiazolium bromide, 27 ml (200 mmol) of triethylamine and 3.9 g (13 mmol) of 4-fluorobenzaldehyde were mixed in 115 ml of methylene chloride at room temperature and then heated at 35° C. for 3 h. After reaction of the aldehyde was complete, 50 ml of saturated ammonium chloride solution were added, and the reaction mixture was stirred for 10 minutes. After removal of the aqueous phase, the organic phase was washed with 0.5 M sodium hydroxide solution and saturated sodium chloride solution. Drying of the organic phase over magnesium sulfate and concentration resulted in a semisolid residue which was stirred with 50 ml of diethyl ether. Filtration of the solid residue by suction resulted in 3.2 g of tert-butyl [2-(4-fluorophenyl)-2-oxo-1-quinolin-8-ylethyl]carbamate.

後処理

  1. customAfter removal of the aqueous phase
  2. washthe organic phase was washed with 0.5 M sodium hydroxide solution and saturated sodium chloride solution
  3. dry with materialDrying of the organic phase over magnesium sulfate and concentration
  4. customresulted in a semisolid residue which
  5. filtrationFiltration of the solid residue by suction
  6. customresulted in 3.2 g of tert-butyl [2-(4-fluorophenyl)-2-oxo-1-quinolin-8-ylethyl]carbamate

出典と根拠

ORDレコード
ord-0c76f965e8944c7ba56e3352bd6e881b
出典データセット
uspto-grants-2010_11
特許番号
US07825264B2

反応ノート

読み込み中…