2,4,6-Trimethylaniline → HCID 11785596, compound

HRID 1796333Notes

Reaction equation

HRID 1796333 reaction equation
Cl[C:2]1[C:7]([S:8]([C:11]2[CH:16]=[CH:15][C:14]([CH2:17][OH: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.O>[CH3:19][C:4]1[N:3]=[C:2]([NH:23][C:22]2[C:24]([CH3:29])=[CH:25][C:26]([CH3:28])=[CH:27][C:21]=2[CH3:20])[C:7]([S:8]([C:11]2[CH:16]=[CH:15][C:14]([CH2:17][OH:18])=[CH:13][CH:12]=2)(=[O:10])=[O:9])=[CH:6][CH:5]=1.[CH3:19][C:4]1[N:3]=[C:2]([NH:23][C:22]2[C:24]([CH3:29])=[CH:25][C:26]([CH3:28])=[CH:27][C:21]=2[CH3:20])[C:7]([S:8]([C:11]2[CH:16]=[CH:15][C:14]([CH2:17][NH:23][C:22]3[C:24]([CH3:29])=[CH:25][C:26]([CH3:28])=[CH:27][C:21]=3[CH3:20])=[CH:13][CH:12]=2)(=[O:10])=[O:9])=[CH:6][CH:5]=1

Participants

6

Reactant 2

HCID 69132,4,6-TrimethylanilineHCID 22181673HCID 22181673, compound

Product 2

HCID 11395370HCID 11395370, compoundHCID 11785596HCID 11785596, compoundYield 5.3%

Reagents, catalysts & solvents 2

HCID 174Ethylene GlycolSolventHCID 962WaterSolvent

Procedure

[4-(2-Chloro-6-methylpyridine-3-sulfonyl)-phenyl]-methanol (1.15 g, 3.86 mmol) and 2,4,6-trimethyl aniline (3.13 g, 23.2 mmol) were heated at reflux in ethylene glycol (3.5 mL) for 16 h. After cooling the mixture was diluted with water (50 mL) and extracted with ethyl acetete (2×200 mL). The combined organic extracts were washed with brine, dried and stripped in vacuo. The residue was purified by column chromatography on silica gel (40% EtOAc/hexanes eluent) to give the product {4-[6-methyl-2-(2,4,6-trimethylphenylamino)-pyridine-3-sulfonyl]-phenyl}-methanol as an amorphous solid (836 mg, 55% yield for the two steps) and (6-methyl-3-{4-[(2,4,6-trimethylphenylamino)-methyl]-benzenesulfonyl}-pyridin-2-yl)-(2,4,6-trimethyl-phenyl)-amine (53 mg, 3.5% yield). mass spec. (AP+): m/z 397 (M+1).

Workup

  1. temperatureAfter cooling the mixture
  2. extractionextracted with ethyl acetete (2×200 mL)
  3. washThe combined organic extracts were washed with brine
  4. customdried
  5. customThe residue was purified by column chromatography on silica gel (40% EtOAc/hexanes eluent)

Sources & evidence

ORD record
ord-4c012cf948594cdea7f422fcc949aa79
Source dataset
uspto-grants-2006_04
Patent number
US07030145B2

Reaction notes

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