Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1) → HCID 89498414, compound

HRID 1430224Notes

Reaction equation

HRID 1430224 reaction equation
[CH2:1]([N:8]([C:23]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24])[NH:9][CH2:10][CH2:11][C:12]1([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)OCC[O:13]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C1(C)C=CC(S([O-])(=O)=O)=CC=1.[NH+]1C=CC=CC=1>CC(C)=O.O.C(OCC)(=O)C>[CH2:1]([N:8]([C:23]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24])[NH:9][CH2:10][CH2:11][C:12](=[O:13])[C:17]1[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 2

HCID 466102Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1)HCID 89498631HCID 89498631, compound

Product 1

HCID 89498414HCID 89498414, compound

Reagents, catalysts & solvents 3

HCID 180AcetoneSolventHCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
100 °C

Procedure

To a solution of EXAMPLE 65C (3.86 g) in acetone (5 mL) and water (5 mL) was added pyridinium p-toluenesulfonate (120 mg). The mixture was stirred at 100° C. in a Biotage Initiator microwave reactor for 10 minutes. The mixture was diluted with ethyl acetate (200 mL) and washed with water and brine and dried over Na2SO4. Filtration and evaporation of the solvent gave the crude product which was used without further purification in the next reaction.

Workup

  1. washwashed with water and brine
  2. dry with materialdried over Na2SO4
  3. filtrationFiltration and evaporation of the solvent

Sources & evidence

ORD record
ord-2d41d49a73b04887963bec7659cbc4d8
Source dataset
uspto-grants-2015_01
Patent number
US08940737B2

Reaction notes

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