p-Toluenesulfonic acid → HCID 22630863, compound

HRID 2416510Notes

Reaction equation

HRID 2416510 reaction equation
C[O:2][CH:3](OC)[C:4]1[CH:9]=[CH:8][C:7]([C:10]2[O:11][CH:12]=[N:13][N:14]=2)=[CH:6][CH:5]=1.C1(C)C=CC(S(O)(=O)=O)=CC=1>O1CCCC1.O>[O:11]1[CH:12]=[N:13][N:14]=[C:10]1[C:7]1[CH:6]=[CH:5][C:4]([CH:3]=[O:2])=[CH:9][CH:8]=1

Participants

4

Reactant 2

HCID 6101p-Toluenesulfonic acidHCID 22631214HCID 22631214, compound

Product 1

HCID 22630863HCID 22630863, compoundYield 72%

Reagents, catalysts & solvents 1

HCID 21881883Oxolane--water (1/1)Solvent

Procedure

To the product from step B (175 mg, 0.80 mmol) in a 1:1 mixture of tetrahydrofuran/water (2 mL) at room temperature was added p-toluenesulfonic acid (50 mg, 0.3 mmol). The reaction mixture was stirred at room temperature for 1 h, and partitioned between dichloromethane and sat. aq. NaHCO3. The organic layer was dried with Na2SO4, and concentrated in vacuo to give 100 mg (72%) of the title product, which was used without further purification. MS 175 (M+H)+.

Workup

  1. custompartitioned between dichloromethane and sat. aq. NaHCO3
  2. dry with materialThe organic layer was dried with Na2SO4
  3. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-f806d48a5f7f4ab3aaffcf3af5ca9584
Source dataset
uspto-grants-2004_11
Patent number
US06825170B2

Reaction notes

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