4-Toluenesulfonyl chloride → HCID 10314366, compound

HRID 1373929Notes

Reaction equation

HRID 1373929 reaction equation
[CH2:1]([O:3][CH2:4][C:5]1[N:6]([N:18]2[CH2:23][CH2:22][O:21][CH2:20][CH2:19]2)[C:7]2[C:16]3[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=3[N:10]=[CH:9][C:8]=2[N:17]=1)[CH3:2].C1C=C(Cl)C=C(C(OO)=O)C=1.[NH4+:35].[OH-].C1(C)C=CC(S(Cl)(=O)=O)=CC=1>C(Cl)Cl.O.CO.C(Cl)(Cl)Cl>[CH2:1]([O:3][CH2:4][C:5]1[N:6]([N:18]2[CH2:19][CH2:20][O:21][CH2:22][CH2:23]2)[C:7]2[C:16]3[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=3[N:10]=[C:9]([NH2:35])[C:8]=2[N:17]=1)[CH3:2]

Participants

9

Reactant 4

HCID 73974-Toluenesulfonyl chlorideHCID 14923Ammonium HydroxideHCID 70297m-Chloroperbenzoic acidHCID 21075717HCID 21075717, compound

Product 1

HCID 10314366HCID 10314366, compound

Reagents, catalysts & solvents 4

HCID 887MethanolSolventHCID 962WaterSolventHCID 6212ChloroformSolventHCID 6344DichloromethaneSolvent2×

Procedure

A solution of 2-ethoxymethyl-1-(morpholin-4-yl)-1H-imidazo[4,5-c]quinoline (1.61 g, 5.51 mmol) in 40 mL of CH2Cl2 was treated with MCPBA (1.78 g, 6.70 mmol, 77% max). After 30 min, the reaction mixture was treated with 20 mL of concentrated NH4OH solution and p-toluenesulfonyl chloride (1.03 g, 5.41 mmol). After 15 min, the reaction mixture was diluted with CH2Cl2 and water and the phases were separated. The organic portion was washed with 5% Na2CO3 solution, water and brine, dried over Na2SO4, filtered and concentrated under reduced pressure to yield a tan foam. Chromatography (SiO2, 97:3 CHCl3:MeOH) gave a light yellow foam. The foam was triturated with diethyl ether and filtered to give 2-ethoxymethyl-1-(morpholin-4-yl)-1H-imidazo[4,5-c]quinolin-4-amine (0.794 g) as a light cream colored solid. mp 223–224° C.;

Workup

  1. waitAfter 15 min
  2. customthe phases were separated
  3. washThe organic portion was washed with 5% Na2CO3 solution, water and brine
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customto yield a tan foam
  8. customThe foam was triturated with diethyl ether
  9. filtrationfiltered

Sources & evidence

ORD record
ord-30695e8ec7464fa1b8271f5a22bd6255
Source dataset
uspto-grants-2007_01
Patent number
US07163947B2

Reaction notes

Loading…