Sodium Carbonate → 4-[6-Methyl-2-(2,4,6-trimethylphenylamino)-pyridine-3-sulfonyl]-phenol

HRID 1796328Notes

Reaction equation

HRID 1796328 reaction equation
C[O:2][C:3]1[CH:8]=[CH:7][C:6]([S:9]([C:12]2[C:13]([NH:19][C:20]3[C:25]([CH3:26])=[CH:24][C:23]([CH3:27])=[CH:22][C:21]=3[CH3:28])=[N:14][C:15]([CH3:18])=[CH:16][CH:17]=2)(=[O:11])=[O:10])=[CH:5][CH:4]=1.C([O-])([O-])=O.[Na+].[Na+]>Br.O>[CH3:18][C:15]1[N:14]=[C:13]([NH:19][C:20]2[C:25]([CH3:26])=[CH:24][C:23]([CH3:27])=[CH:22][C:21]=2[CH3:28])[C:12]([S:9]([C:6]2[CH:5]=[CH:4][C:3]([OH:2])=[CH:8][CH:7]=2)(=[O:11])=[O:10])=[CH:17][CH:16]=1

Participants

5

Reactant 2

HCID 10340Sodium CarbonateHCID 11474959N-mesityl-3-(4-methoxyphenylsulfonyl)-6-methylpyridin-2-amine

Product 1

HCID 112112464-[6-Methyl-2-(2,4,6-trimethylphenylamino)-pyridine-3-sulfonyl]-phenolYield 89.8%

Reagents, catalysts & solvents 2

HCID 260Hydrogen BromideSolventHCID 962WaterSolvent

Procedure

[3-(4-Methoxybenzenesulfonyl)-6-methyl-pyridin-2-yl]-(2,4,6-trimethylphenyl)-amine from Example 9 (3.0 g, 7.57 mmol) was heated in 48% HBr (40 mL) at 110° C. for 48 h. After cooling it was diluted with water (100 mL) and neutralized with Na2CO3. Then it was extracted with EtOAc (3×100 mL each) and the combined organic extracts were dried and stripped in vacuo. The residue was washed with ether to give 4-[6-methyl-2-(2,4,6-trimethylphenylamino)-pyridine-3-sulfonyl]-phenol as a solid (2.6 g), mp 226–228° C. mass spec. (AP+): m/z 383 (M+1).

Workup

  1. temperatureAfter cooling it
  2. extractionThen it was extracted with EtOAc (3×100 mL each)
  3. customthe combined organic extracts were dried
  4. washThe residue was washed with ether

Sources & evidence

ORD record
ord-96a6e10a4b2349fa9554c5dc892258af
Source dataset
uspto-grants-2006_04
Patent number
US07030145B2

Reaction notes

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