Hydrochloric Acid → HCID 621095, compound

HRID 1836612Notes

Reaction equation

HRID 1836612 reaction equation
[CH3:1][C:2]1[C:15]2[NH:14][S:13](=[O:17])(=[O:16])[C:12]3[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=3)[C:6]=2[C:5]([CH3:18])=[CH:4][CH:3]=1.[C:19]1([CH3:29])[CH:24]=[CH:23][C:22]([S:25](Cl)(=[O:27])=[O:26])=[CH:21][CH:20]=1.Cl>N1C=CC=CC=1>[CH3:1][C:2]1[C:15]2[N:14]([S:25]([C:22]3[CH:23]=[CH:24][C:19]([CH3:29])=[CH:20][CH:21]=3)(=[O:27])=[O:26])[S:13](=[O:17])(=[O:16])[C:12]3[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=3)[C:6]=2[C:5]([CH3:18])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 73974-Toluenesulfonyl chlorideHCID 5227075HCID 5227075, compound

Product 1

HCID 621095HCID 621095, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Conditions

Temperature
60 °C

Procedure

1,4-Dimethyl-10H-9-thia-10-aza-phenanthrene 9,9-dioxide (2.6 g, 10 mmol) is dissolved in pyridine (10 mL) and treated with p-toluenesulfonyl chloride (2.8 g, 15 mmol). The reaction mixture stirred at 60° C. until TLC shows disappearance of the starting material. The reaction mixture is allowed to cool and then poured into 100 mL of 3N HCl. The mixture is extracted 2×100 mL EtOAc and the combined organic layers are washed with sat. brine, dried over MgSO4, filtered, and concentrated to a solid, which is recrystallized from hot EtOAc/hexanes to give 1,4-dimethyl-10-(toluene-4-sulfonyl)-10H-9-thia-10-aza-phenanthrene 9,9-dioxide.

Workup

  1. temperatureto cool
  2. extractionThe mixture is extracted 2×100 mL EtOAc
  3. washthe combined organic layers are washed with sat. brine
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated to a solid, which
  7. customis recrystallized from hot EtOAc/hexanes

Sources & evidence

ORD record
ord-24772378bcd548c89f7e3cc98722fa42
Source dataset
uspto-grants-2004_08
Patent number
US06777446B2

Reaction notes

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