p-Toluenesulfonic acid → HCID 86759330, compound

HRID 2120285Notes

Reaction equation

HRID 2120285 reaction equation
[C:1]([O:5][C:6]([N:8]1[C@H:15]2[CH2:16][C@H:11]([CH2:12][CH2:13][C@@H:14]2[N:17]2[CH:25]=[N:24][C:23]3[C:18]2=[N:19][CH:20]=[N:21][C:22]=3[N:26]=CN(C)C)[CH2:10][C:9]1=[O:31])=[O:7])([CH3:4])([CH3:3])[CH3:2].C1(C)C=CC(S(NN)(=O)=O)=CC=1.CC1C=CC(S(O)(=O)=O)=CC=1>C(Cl)Cl>[C:1]([O:5][C:6]([N:8]1[C@H:15]2[CH2:16][C@H:11]([CH2:12][CH2:13][C@@H:14]2[N:17]2[CH:25]=[N:24][C:23]3[C:18]2=[N:19][CH:20]=[N:21][C:22]=3[NH2:26])[CH2:10][C:9]1=[O:31])=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 6101p-Toluenesulfonic acidHCID 15303P-ToluenesulfonylhydrazideHCID 86759331HCID 86759331, compound

Product 1

HCID 86759330HCID 86759330, compoundYield 86%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A 250 ml round-bottomed flask was loaded with 6.64 g of amidine A lactam 15d (15.5 mmol) and 150 ml of dry CH2Cl2. 11.55 g of p-toluenesulphonic acid hydrazide (62.0 mmol) were then added followed by 1.47 g of TsOH (7.75 mmol). The solution was stirred at room temperature for 44 h. After the addition of 150 ml of CH2Cl2, the solution was washed three times with water and adjusted to a pH of >12 by addition of 2M NaOH. The combined wash solutions were extracted with 100 ml of CH2Cl2 and the combined organic phases dried over MgSO4. After filtration, the solvent was removed under reduced pressure and the resulting residue was purified by means of chromatography (5.2×20 cm silica gel, eluent: CHCl3/MeOH 30:1) to afford 4.96 g of 15e (86%), which is sufficiently pure for further reactions. An analytical sample was obtained by crystallization from THF/cyclohexane.

Workup

  1. washthe solution was washed three times with water
  2. additionadjusted to a pH of >12 by addition of 2M NaOH
  3. washThe combined wash solutions
  4. extractionwere extracted with 100 ml of CH2Cl2
  5. dry with materialthe combined organic phases dried over MgSO4
  6. filtrationAfter filtration
  7. customthe solvent was removed under reduced pressure
  8. customthe resulting residue was purified by means of chromatography (5.2×20 cm silica gel, eluent: CHCl3/MeOH 30:1)

Sources & evidence

ORD record
ord-5a66c77f5df543738346d76082bb18b1
Source dataset
uspto-grants-2004_02
Patent number
US06689884B1

Reaction notes

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