Dimethyl Sulfide → HCID 15631837, compound

HRID 1722281Notes

Reaction equation

HRID 1722281 reaction equation
[N+:1]([C:4]1[CH:10]=[C:9]([F:11])[C:8]([F:12])=[CH:7][C:5]=1[NH2:6])([O-:3])=[O:2].[CH3:13][S:14][CH3:15].ClN1C(=O)CCC1=O.C(N(CC)CC)C>ClCCl>[N+:1]([C:4]1[CH:10]=[C:9]([F:11])[C:8]([F:12])=[C:7]([CH2:13][S:14][CH3:15])[C:5]=1[NH2:6])([O-:3])=[O:2]

Participants

6

Reactant 4

HCID 1068Dimethyl SulfideHCID 8471TriethylamineHCID 31398ChlorosuccinimideHCID 1571514,5-Difluoro-2-nitroaniline

Product 1

HCID 15631837HCID 15631837, compoundYield 34.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 2-nitro-4,5-difluoroaniline (1.0 g) and dimethylsulfide (1.79 g) in dichloromethane (40 ml) is added gradually N-chlorosuccinimide (3.82 g) with stirring at below 15° C. The mixture is stirred for 30 minutes, and thereto is added triethylamine (2.89 g), and the mixture is refluxed for 21 hours. After allowing to cool, the reaction mixture is washed with 10% aqueous sodium hydroxide, water and aqueous sodium chloride in this order and dried. The solvent is removed by concentration, and the resulting residue is purified by silica gel column chromatography (solvent, n-hexane:ethylacetate=30:1) and then recrystallized from n-nexane to give 2-nitro-4,5-difluoro-6-methylthiomethylaniline (0.47 g) as yellow needles, m.p. 110°-111.5° C.

Workup

  1. stirringThe mixture is stirred for 30 minutes
  2. temperaturethe mixture is refluxed for 21 hours
  3. temperatureto cool
  4. washthe reaction mixture is washed with 10% aqueous sodium hydroxide, water and aqueous sodium chloride in this order
  5. customdried
  6. customThe solvent is removed by concentration
  7. customthe resulting residue is purified by silica gel column chromatography (solvent, n-hexane:ethylacetate=30:1)
  8. customrecrystallized from n-nexane

Sources & evidence

ORD record
ord-5c22ddd35dbc4b0f8066fb2e0ce76a97
Source dataset
uspto-grants-1989_08
Patent number
US04855292

Reaction notes

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