p-Toluenesulfonic acid → HCID 22267336, compound

HRID 275696Notes

Reaction equation

HRID 275696 reaction equation
[CH3:1][C:2]1[N:3]=[C:4]([N:20]([CH2:24][CH2:25][CH3:26])[CH2:21][CH2:22][CH3:23])[C:5]2[N:11]=[CH:10]N=[C:8]([C:12]3[CH:17]=[CH:16][C:15]([Cl:18])=[CH:14][C:13]=3[Cl:19])[C:6]=2[N:7]=1.[C:27]1(C)C=CC(S(O)(=O)=O)=CC=1.C(NCCC)CC>O.CCOC(C)=O>[CH3:1][C:2]1[N:3]=[C:4]([N:20]([CH2:21][CH2:22][CH3:23])[CH2:24][CH2:25][CH3:26])[C:5]2[N:11]=[CH:10][CH:27]=[C:8]([C:12]3[CH:17]=[CH:16][C:15]([Cl:18])=[CH:14][C:13]=3[Cl:19])[C:6]=2[N:7]=1

Participants

6

Reactant 3

HCID 6101p-Toluenesulfonic acidHCID 8902DipropylamineHCID 70168795HCID 70168795, compound

Product 1

HCID 22267336HCID 22267336, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
195 °C

Procedure

A mixture of 4 (10 mg), p-toluenesulfonic acid (20 mg) and dipropylamine (50 ml) is stirred and heated to 195° C. in a sealed tube for 1.5 h. The solution is then allowed to cool to r.t., and dissolved in a mixture of water and EtOAc. This is extracted with EtOAc, the organic phase washed with brine, dried and concentrated. The product is purified by prep. TLC (SiO2) using ethyl acetate/hexane.

Workup

  1. temperatureto cool to r.t.
  2. extractionThis is extracted with EtOAc
  3. washthe organic phase washed with brine
  4. customdried
  5. concentrationconcentrated
  6. customThe product is purified by prep

Sources & evidence

ORD record
ord-4a06962552d3482098bb7b99ea47eb75
Source dataset
uspto-grants-2002_03
Patent number
US06352990B1

Reaction notes

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