Sodium hydride → HCID 19870524, compound

HRID 330029Notes

Reaction equation

HRID 330029 reaction equation
[H-].[Na+].[SH:3][C:4]1[CH:13]=[CH:12][C:7]([C:8]([O:10][CH3:11])=[O:9])=[CH:6][CH:5]=1.Cl[CH:15]([C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=1[C:28]([F:31])([F:30])[F:29])[CH2:16][N:17]1[CH:21]=[CH:20][N:19]=[CH:18]1>CN(C)C=O>[F:31][C:28]([F:29])([F:30])[C:23]1[CH:24]=[CH:25][CH:26]=[CH:27][C:22]=1[CH:15]([S:3][C:4]1[CH:5]=[CH:6][C:7]([C:8]([O:10][CH3:11])=[O:9])=[CH:12][CH:13]=1)[CH2:16][N:17]1[CH:21]=[CH:20][N:19]=[CH:18]1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 237573Methyl 4-sulfanylbenzoateHCID 19870507HCID 19870507, compound

Product 1

HCID 19870524HCID 19870524, compoundYield 73.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

374 mg of a 55% w/w suspension of sodium hydride in mineral oil were added to 1.44 g of methyl 4-mercaptobenzoate in 9.1 mg of dry dimethylformamide, whilst ice-cooling, and the resulting mixture was stirred at room temperature for 30 minutes. 2.14 g of 1-[2-chloro-2-(2-trifluoromethylphenyl)ethyl]imidazole in 11.2 ml of dry dimethylformamide were added to this solution, and the resulting mixture were heated at 60°-70° C. for 6 hours. At the end of this time, the reaction mixture was treated and purified by the same method as described in Example 1, to give 2.34 g of the title compound as white cyrstals, melting at 121°-126° C.

Workup

  1. temperaturecooling
  2. temperaturethe resulting mixture were heated at 60°-70° C. for 6 hours
  3. additionAt the end of this time, the reaction mixture was treated
  4. custompurified by the same method

Sources & evidence

ORD record
ord-ce271a856431487c9cb732e6f3daaf0f
Source dataset
uspto-grants-1990_01
Patent number
US04894385

Reaction notes

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