Water → HCID 69521228, compound

HRID 856691Notes

Reaction equation

HRID 856691 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([SH:10])=[C:6]([C:11]([F:14])([F:13])[F:12])[CH:5]=1)([O-:3])=[O:2].C(N(CC)CC)C.Cl.Cl[CH2:24][C:25]1[CH:26]=[N:27][CH:28]=[CH:29][CH:30]=1.O>C1COCC1>[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([S:10][CH2:24][C:25]2[CH:26]=[N:27][CH:28]=[CH:29][CH:30]=2)=[C:6]([C:11]([F:14])([F:12])[F:13])[CH:5]=1)([O-:3])=[O:2]

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 233943-(Chloromethyl)pyridine hydrochlorideHCID 4713007HCID 4713007, compound

Product 1

HCID 69521228HCID 69521228, compoundYield 52.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

4-nitro-2-(trifluoromethyl)benzenethiol (3.0 g) was dissolved in THF (60 ml), and to this solution was added triethylamine (5.25 ml) and then, 3-(chloromethyl)pyridine hydrochloride (2.65 g), and the mixture was stirred for 1 hour at room temperature. The reaction solution was added to water, and extracted with ethyl acetate. The organic layer was washed with saturated brine, and dried over magnesium sulfate. The solvent was removed under reduced pressure and the obtained residue was washed with hexane/ethyl acetate, to give 3-[[[4-nitro-2-(trifluoromethyl)phenyl]sulfanyl]methyl]pyridine (2.2 g).

Workup

  1. extractionextracted with ethyl acetate
  2. washThe organic layer was washed with saturated brine
  3. dry with materialdried over magnesium sulfate
  4. customThe solvent was removed under reduced pressure
  5. washthe obtained residue was washed with hexane/ethyl acetate

Sources & evidence

ORD record
ord-40aa56f57ec54d4da74baa9e559f6541
Source dataset
uspto-grants-2007_08
Patent number
US07262185B2

Reaction notes

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