p-Toluenesulfonic acid → HCID 59342358, compound

HRID 15730

Reaction equation

HRID 15730 reaction equation
[CH:1]([C:3]1[CH:4]=[N:5][CH:6]=[N:7][CH:8]=1)=O.[Cl:9][C:10]1[CH:15]=[CH:14][C:13]([S:16]([NH2:19])(=[O:18])=[O:17])=[CH:12][CH:11]=1.CC1C=CC(S(O)(=O)=O)=CC=1>C1(C)C=CC=CC=1>[Cl:9][C:10]1[CH:11]=[CH:12][C:13]([S:16](/[N:19]=[CH:1]/[C:3]2[CH:4]=[N:5][CH:6]=[N:7][CH:8]=2)(=[O:17])=[O:18])=[CH:14][CH:15]=1

Participants

5

Reactant 3

HCID 6101p-Toluenesulfonic acidHCID 668244-ChlorobenzenesulfonamideHCID 2761034Pyrimidine-5-carboxaldehyde

Product 1

HCID 59342358HCID 59342358, compoundYield 81%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a solution of 5-formyl pyrimidine (68, 1.0 g, 9.3 mmol) and 4-chlorobenzene sulfonamide (1.95 g, 10.2 mmol) in toluene (20 mL) was added 4 Å molecular sieves (1.0 g) and MP-TsOH (1.0 g). Dean-stark apparatus with reflux condenser was affixed to reaction vessel and reaction was heated at reflux for 18 hours. The reaction mixture was cooled to room temperature and concentrated in vacuo. The residue was taken up in EtOAc and filtered through Celite. The filtrate was concentrated in vacuo to yield 2.12 g (81%) 69 as a light brown solid, 1H NMR (CDCl3) δ 9.42 (s, 1H), 9.25 (s, 2H), 9.15 (s, 1H), 7.98 (d, 2H), 7.57 (d, 2H).

Workup

  1. temperatureDean-stark apparatus with reflux condenser
  2. customwas affixed to reaction vessel and reaction
  3. temperaturewas heated
  4. temperatureat reflux for 18 hours
  5. concentrationconcentrated in vacuo
  6. filtrationfiltered through Celite
  7. concentrationThe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-ee9130598be74c03a5d2ba3e8c103572
Source dataset
uspto-grants-2010_06
Patent number
US07732609B2

Linked notes

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