Water → HCID 69288501, compound

HRID 1392371Notes

Reaction equation

HRID 1392371 reaction equation
C([C:3]1([C:19]2[CH:24]=[CH:23][C:22]([Cl:25])=[CH:21][CH:20]=2)[S:7][CH:6]([C:8]([O-:10])=O)[N:5]=[C:4]1[C:11]1[CH:16]=[CH:15][C:14]([Cl:17])=[CH:13][C:12]=1[Cl:18])C.[NH2:26][C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1.C[Si](C)(C)[N-][Si](C)(C)C.[Na+].O>C1COCC1>[Cl:25][C:22]1[CH:23]=[CH:24][C:19]([C:3]2[S:7][C:6]([C:8]([NH:26][C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=3)=[O:10])=[N:5][C:4]=2[C:11]2[CH:16]=[CH:15][C:14]([Cl:17])=[CH:13][C:12]=2[Cl:18])=[CH:20][CH:21]=1

Participants

6

Reactant 4

HCID 962WaterHCID 6115AnilineHCID 2724254Sodium bis(trimethylsilyl)amideHCID 86595684HCID 86595684, compound

Product 1

HCID 69288501HCID 69288501, compoundYield 77.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
0 °C

Procedure

5-Ethyl-5-(4-chlorophenyl)-4-(2,4-dichlorophenyl)thiazole-2-carboxylate (1.65 gram, 4.0 mmol) is dissolved in anhydrous THF (25 mL) and aniline (0.37 mL, 4.0 mmol) is added. The resulting solution is cooled to 0° C. and sodium hexamethyidisilazide (4.4 mL of a 1M solution in THF) is added. The reaction mixture is stirred for 2 hours. Water is added and the mixture is extracted twice with ethyl acetate. The combined organic layer is washed with brine, dried over MgSO4, filtered and concentrated in vacuo. The residue is crystallised from diisopropyl ether to give 5-(4-chlorophenyl)-4-(2,4-dichlorophenyl)-N-phenyl-thiazole-2-carboxamide (1.42 g, 77% yield). Melting point: 167-168° C.

Workup

  1. extractionthe mixture is extracted twice with ethyl acetate
  2. washThe combined organic layer is washed with brine
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe residue is crystallised from diisopropyl ether

Sources & evidence

ORD record
ord-de1ff402f6a441a2ba2f338822060276
Source dataset
uspto-grants-2008_03
Patent number
US07342032B2

Reaction notes

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