4-Toluenesulfonyl chloride → HCID 58833695, compound

HRID 540871Notes

Reaction equation

HRID 540871 reaction equation
[CH3:1][S:2]([O:5][C:6]1[CH:7]=[CH:8][C:9]2[C:10]3[N:18]([CH2:19][CH2:20][O:21][C:22]4[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=4)[C:17]([CH2:28][CH3:29])=[N:16][C:11]=3[CH:12]=[N:13][C:14]=2[CH:15]=1)(=[O:4])=[O:3].ClC1C=C(C=CC=1)C(OO)=O.[OH-].[NH4+:42].C1(C)C=CC(S(Cl)(=O)=O)=CC=1>C(Cl)(Cl)Cl>[CH3:1][S:2]([O:5][C:6]1[CH:7]=[CH:8][C:9]2[C:10]3[N:18]([CH2:19][CH2:20][O:21][C:22]4[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=4)[C:17]([CH2:28][CH3:29])=[N:16][C:11]=3[C:12]([NH2:42])=[N:13][C:14]=2[CH:15]=1)(=[O:3])=[O:4]

Participants

6

Reactant 4

HCID 73974-Toluenesulfonyl chlorideHCID 14923Ammonium HydroxideHCID 70297m-Chloroperbenzoic acidHCID 86611426HCID 86611426, compound

Product 1

HCID 58833695HCID 58833695, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

2-Ethyl-1-(2-phenoxyethyl)-1H-imidazo[4,5-c]quinolin-7-yl methanesulfonate (0.625 g, 1.52 mmol) was dissolved in chloroform (15 mL). 3-Chloroperoxybenzoic acid (60% pure, 0.437 g, 1.52 mmol) was added in one portion, and the reaction was stirred for 25 minutes. Ammonium hydroxide (25 mL) was added. A precipitate formed, and the reaction was stirred until the precipitate dissolved. p-Toluenesulfonyl chloride (0.290 g, 1.52 mmol) was added in one portion, and the reaction mixture was stirred for an additional 16 hours. The layers were separated, and the aqueous fraction was extracted with dichloromethane followed by chloroform. The organics were combined, washed sequentially with water and brine, dried over sodium sulfate, filtered and concentrated under reduced pressure. Purification by column chromatography on silica gel (eluting with a chloroform:methanol:ammonium hydroxide gradient) followed by recrystallization from acetonitrile provided 0.150 g of 4-amino-2-ethyl-1-(2-phenoxyethyl)-1H-imidazo[4,5-c]quinolin-7-yl methanesulfonate as an orange solid, mp 213.0-214.5° C.

Workup

  1. customA precipitate formed
  2. stirringthe reaction was stirred until the precipitate
  3. dissolutiondissolved
  4. stirringthe reaction mixture was stirred for an additional 16 hours
  5. customThe layers were separated
  6. extractionthe aqueous fraction was extracted with dichloromethane
  7. washwashed sequentially with water and brine
  8. dry with materialdried over sodium sulfate
  9. filtrationfiltered
  10. concentrationconcentrated under reduced pressure
  11. customPurification by column chromatography on silica gel (
  12. washeluting with a chloroform
  13. custommethanol:ammonium hydroxide gradient) followed by recrystallization from acetonitrile

Sources & evidence

ORD record
ord-09640d5298d641c8947356544706d3e3
Source dataset
uspto-grants-2014_10
Patent number
US08871782B2

Reaction notes

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