Water → HCID 19919984, compound

HRID 1648414Notes

Reaction equation

HRID 1648414 reaction equation
[H-].[Na+].[Cl:3][C:4]1[C:5]([SH:14])=[N:6][CH:7]=[C:8]([C:10]([F:13])([F:12])[F:11])[CH:9]=1.[N+:15]([C:18]1[CH:25]=[CH:24][CH:23]=[CH:22][C:19]=1[CH2:20]Br)([O-:17])=[O:16].O>O1CCCC1>[Cl:3][C:4]1[C:5]([S:14][CH2:20][C:19]2[CH:22]=[CH:23][CH:24]=[CH:25][C:18]=2[N+:15]([O-:17])=[O:16])=[N:6][CH:7]=[C:8]([C:10]([F:12])([F:13])[F:11])[CH:9]=1

Participants

6

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 77569alpha-Bromo-2-nitrotolueneHCID 178506245HCID 178506245, compound

Product 1

HCID 19919984HCID 19919984, compoundYield 74.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Procedure

2 g of 60 wt % sodium hydride were added to 45 ml of tetrahydrofuran under stirring at room temperature, followed by drop-wise addition thereto of a solution of 9.9 g of 3-chloro-2-mercapto-5-trifluoromethylpyridine in 40 ml of tetrahydrofuran. After completion of the drop-wise addition, the reaction mixture was heated under reflux for 30 minutes, and cooled to room temperature, followed by drop-wise addition thereto of a solution of 10 g of 2-nitrobenzyl bromide in 60 ml of tetrahydrofuran. After completion of the drop-wise addition, stirring was continued at room temperature for 15 hours. The reaction mixture was poured into water, subjected to extraction with ethyl acetate, washed with water, and dried over anhydrous sodium sulfate. The solvent was distilled off under reduced pressure. The resulting residue was purified by silica gel column chromatography (developing solvent:methylene chloride:hexane=4:1) to obtain 12 g of 2-(3-chloro-5-trifluoromethyl-2-pyridylthiomethyl)nitrobenzene.

Workup

  1. additionfollowed by drop-wise addition
  2. additionAfter completion of the drop-wise addition
  3. temperaturethe reaction mixture was heated
  4. temperatureunder reflux for 30 minutes
  5. temperaturecooled to room temperature
  6. additionfollowed by drop-wise addition
  7. additionAfter completion of the drop-wise addition
  8. stirringstirring
  9. extractionsubjected to extraction with ethyl acetate
  10. washwashed with water
  11. dry with materialdried over anhydrous sodium sulfate
  12. distillationThe solvent was distilled off under reduced pressure
  13. customThe resulting residue was purified by silica gel column chromatography (developing solvent:methylene chloride:hexane=4:1)

Sources & evidence

ORD record
ord-e1a7daa5c4364cf681b0deb1acd2bb8a
Source dataset
uspto-grants-1995_07
Patent number
US05436267

Reaction notes

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