4-Toluenesulfonyl chloride → HCID 58923895, compound

HRID 1364025Notes

Reaction equation

HRID 1364025 reaction equation
[OH-].[NH4+:2].[CH3:3][C:4]1([CH3:26])[CH2:21][N:8]2[C:9]3[C:18]4[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=4)[N+:12]([O-])=[CH:11][C:10]=3[N:20]=[C:7]2[CH2:6][N:5]1[S:22]([CH3:25])(=[O:24])=[O:23].C1(C)C=CC(S(Cl)(=O)=O)=CC=1>ClCCl>[CH3:3][C:4]1([CH3:26])[CH2:21][N:8]2[C:9]3[C:18]4[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=4)[N:12]=[C:11]([NH2:2])[C:10]=3[N:20]=[C:7]2[CH2:6][N:5]1[S:22]([CH3:25])(=[O:24])=[O:23]

Participants

5

Reactant 3

HCID 73974-Toluenesulfonyl chlorideHCID 14923Ammonium HydroxideHCID 66958640HCID 66958640, compound

Product 1

HCID 58923895HCID 58923895, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Ammonium hydroxide (5 mL) was added with vigorous stirring to a suspension of 10,10-dimethyl-9-(methylsulfonyl)-5-oxido-8,9,10,11-tetrahydropyrazino[1′,2′:1,2]imidazo[4,5-c]quinoline (0.91 g, 2.6 mmol) in dichloromethane (25 mL). p-Toluenesulfonyl chloride (0.50 g, 2.6 mmol) was added in one portion, and the reaction was stirred for four hours at ambient temperature. The organic layer was separated and washed with 1% aqueous sodium carbonate (50 mL) and brine, dried over sodium sulfate, filtered, and concentrated under reduced pressure. The resulting orange solid (0.77 g) was recrystallized from 1,2-dichloroethane to provide 10,10-dimethyl-9-(methylsulfonyl)-8,9,10,11-tetrahydropyrazino[1′,2′:1,2]imidazo[4,5-c]quinolin-6-amine as a white powder, mp 227-228° C.

Workup

  1. customThe organic layer was separated
  2. washwashed with 1% aqueous sodium carbonate (50 mL) and brine
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customThe resulting orange solid (0.77 g) was recrystallized from 1,2-dichloroethane

Sources & evidence

ORD record
ord-e2590925e7074ce7aec46709f980425e
Source dataset
uspto-grants-2011_02
Patent number
US07888349B2

Reaction notes

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