Sodium hydride → 5-(4-chlorophenyl)-4-(2,4-dichlorophenyl)-N-(4,4,4-trifluorobutyl)thiazole-2-carboxamide

HRID 1392373ノート

反応式

HRID 1392373 の反応式
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[S:12][C:11]([C:13]([NH2:15])=[O:14])=[N:10][C:9]=2[C:16]2[CH:21]=[CH:20][C:19]([Cl:22])=[CH:18][C:17]=2[Cl:23])=[CH:4][CH:3]=1.[H-].[Na+].[F:26][C:27]([F:33])([F:32])[CH2:28][CH2:29][CH2:30]Br>CN(C=O)C>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[S:12][C:11]([C:13]([NH:15][CH2:30][CH2:29][CH2:28][C:27]([F:33])([F:32])[F:26])=[O:14])=[N:10][C:9]=2[C:16]2[CH:21]=[CH:20][C:19]([Cl:22])=[CH:18][C:17]=2[Cl:23])=[CH:6][CH:7]=1

参加物

5

反応物 3

HCID 24758Sodium hydrideHCID 5210064-Bromo-1,1,1-trifluorobutaneHCID 692892035-(4-Chlorophenyl)4-(2,4-dichlorophenyl)thiazole-2-carboxamide

生成物 1

HCID 865956855-(4-chlorophenyl)-4-(2,4-dichlorophenyl)-N-(4,4,4-trifluorobutyl)thiazole-2-carboxamide

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
0 °C

実験手順

Part B: To a cooled (0° C.) stirred solution of 5-(4-chlorophenyl)-4-(2,4-dichlorophenyl)thiazole-2-carboxamide (1.16 gram, 3.02 mmol) in anhydrous DMF (20 mL) is added NaH (0.13 gram of a 60% dispersion) in a nitrogen atmosphere. The resulting mixture is stirred for 1 hour and excess 4,4,4-trifluoro-1-bromobutane (0.7 mL) is added. The resulting solution is stirred at room temperature for 1 hour, poured onto ice/water and extracted twice with diethyl ether. The collected diethyl ether layers are twice washed with water, dried over Na2SO4, filtered and concentrated in vacuo. The residue is further purified by column chromatography (silica gel: eluant: dichloromethane) to give 5-(4-chlorophenyl)-4-(2,4-dichlorophenyl)-N-(4,4,4-trifluorobutyl)thiazole-2-carboxamide. Melting point: 99-101° C.

後処理

  1. stirringThe resulting solution is stirred at room temperature for 1 hour
  2. additionpoured onto ice/water
  3. extractionextracted twice with diethyl ether
  4. washThe collected diethyl ether layers are twice washed with water
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customThe residue is further purified by column chromatography (silica gel: eluant: dichloromethane)

出典と根拠

ORDレコード
ord-b656c3aea5944e739799f0a1aef0c15b
出典データセット
uspto-grants-2008_03
特許番号
US07342032B2

反応ノート

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