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

HRID 1392373노트

반응식

HRID 1392373 반응식
[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

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

반응 조건

온도
0 °C

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-b656c3aea5944e739799f0a1aef0c15b
출처 데이터셋
uspto-grants-2008_03
특허 번호
US07342032B2

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