4-Toluenesulfonyl chloride → HCID 58970357, compound

HRID 2366645Notes

Reaction equation

HRID 2366645 reaction equation
C1C=C(Cl)C=C(C(OO)=O)C=1.[N:12]1([CH2:25][CH2:26][C:27]([NH:29][CH3:30])=[O:28])[C:24]2[C:23]3[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=3[N:17]=[CH:16][C:15]=2[N:14]=[CH:13]1.[OH-].[NH4+:32].C1(C)C=CC(S(Cl)(=O)=O)=CC=1>C(Cl)(Cl)Cl>[NH2:32][C:16]1[C:15]2[N:14]=[CH:13][N:12]([CH2:25][CH2:26][C:27]([NH:29][CH3:30])=[O:28])[C:24]=2[C:23]2[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=2[N:17]=1

Participants

6

Reactant 4

HCID 73974-Toluenesulfonyl chlorideHCID 14923Ammonium HydroxideHCID 70297m-Chloroperbenzoic acidHCID 57447042HCID 57447042, compound

Product 1

HCID 58970357HCID 58970357, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

mCPBA (8.95 g, 38.9 mmol) was added to a solution of 3-(1H-imidazo[4,5-c]quinolin-1-yl)-N-methylpropanamide (4.4 g, 15.6 mmol) in chloroform (100 mL); the reaction was stirred for one hour at ambient temperature. Ammonium hydroxide (40 mL) was added, and the mixture was stirred vigorously for 15 minutes. p-Toluenesulfonyl chloride (5.94 g, 31.2 mmol) was added over a period of ten minutes, and the reaction was stirred for two hours. The reaction mixture was filtered to remove a precipitate, and the organic layer was separated and washed with saturated aqueous sodium bicarbonate, dried over magnesium sulfate, filtered, and concentrated under reduced pressure. The crude product was recrystallized from methanol to provide 0.535 g of 3-(4-amino-1H-imidazo[4,5-c]quinolin-1-yl)-N-methylpropanamide as off-white needles, mp>260° C.

Workup

  1. stirringthe mixture was stirred vigorously for 15 minutes
  2. stirringthe reaction was stirred for two hours
  3. filtrationThe reaction mixture was filtered
  4. customto remove a precipitate
  5. customthe organic layer was separated
  6. washwashed with saturated aqueous sodium bicarbonate
  7. dry with materialdried over magnesium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated under reduced pressure
  10. customThe crude product was recrystallized from methanol

Sources & evidence

ORD record
ord-b01734e5c1724a008d7faeebd5e66d0c
Source dataset
uspto-grants-2014_04
Patent number
US08697873B2

Reaction notes

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