2,4,6-Trimethylaniline → N-mesityl-3-(4-methoxyphenylsulfonyl)-6-methylpyridin-2-amine

HRID 1796327Notes

Reaction equation

HRID 1796327 reaction equation
Cl[C:2]1[C:7]([S:8]([C:11]2[CH:16]=[CH:15][C:14]([O:17][CH3:18])=[CH:13][CH:12]=2)(=[O:10])=[O:9])=[CH:6][CH:5]=[C:4]([CH3:19])[N:3]=1.[CH3:20][C:21]1[CH:27]=[C:26]([CH3:28])[CH:25]=[C:24]([CH3:29])[C:22]=1[NH2:23]>C(O)CO>[CH3:18][O:17][C:14]1[CH:15]=[CH:16][C:11]([S:8]([C:7]2[C:2]([NH:23][C:22]3[C:24]([CH3:29])=[CH:25][C:26]([CH3:28])=[CH:27][C:21]=3[CH3:20])=[N:3][C:4]([CH3:19])=[CH:5][CH:6]=2)(=[O:10])=[O:9])=[CH:12][CH:13]=1

Participants

4

Reactant 2

HCID 69132,4,6-TrimethylanilineHCID 221816772-Chloro-3-(4-methoxybenzenesulfonyl)-6-methylpyridine

Product 1

HCID 11474959N-mesityl-3-(4-methoxyphenylsulfonyl)-6-methylpyridin-2-amineYield 65.5%

Reagents, catalysts & solvents 1

HCID 174Ethylene GlycolSolvent

Procedure

2-chloro-3-(4-methoxybenzenesulfonyl)-6-methylpyridine (1.6 g, 5.39 mmol) and 2,4,6-trimethylaniline (4.4 g, 32.8 mmol) were heated at reflux in ethylene glycol (5.5 mL) for 20 h. After cooling, the reaction was partitioned between EtOAc (100 mL) and 0.5 N NaOH (20 mL) and the aqueous layer was extracted with EtOAc (100 mL) and the combined organic extracts were washed with water, brine, dried and stripped in vacuo. The residue was chromatographed on silica gel using 20% EtOAc/hexanes as eluent to give [3-(4-methoxybenzenesulfonyl)-6-methyl-pyridin-2-yl]-(2,4,6-trimethylphenyl)-amine as a solid (1.4 g), mp 165–167° C. mass spec. (AP+): m/z 397 (M+1).

Workup

  1. temperatureAfter cooling
  2. customthe reaction was partitioned between EtOAc (100 mL) and 0.5 N NaOH (20 mL)
  3. extractionthe aqueous layer was extracted with EtOAc (100 mL)
  4. washthe combined organic extracts were washed with water, brine
  5. customdried
  6. customThe residue was chromatographed on silica gel using 20% EtOAc/hexanes as eluent

Sources & evidence

ORD record
ord-fdc831fb07a84cea93bb198a1a80acbd
Source dataset
uspto-grants-2006_04
Patent number
US07030145B2

Reaction notes

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