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

HRID 1392373Notes

Reaction equation

HRID 1392373 reaction equation
[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

Participants

5

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
0 °C

Procedure

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.

Workup

  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)

Sources & evidence

ORD record
ord-b656c3aea5944e739799f0a1aef0c15b
Source dataset
uspto-grants-2008_03
Patent number
US07342032B2

Reaction notes

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