Methanesulfonyl chloride → HCID 18940224, compound

HRID 355622Notes

Reaction equation

HRID 355622 reaction equation
[NH2:1][C:2]1[CH:15]=[CH:14][C:13]2[C:4](=[C:5]([C:16]3[CH:21]=[CH:20][C:19]([CH3:22])=[CH:18][CH:17]=3)[C:6]3[C:11]([N:12]=2)=[CH:10][CH:9]=[CH:8][CH:7]=3)[CH:3]=1.[CH3:23][S:24](Cl)(=[O:26])=[O:25].N12CCC(CC1)CN2>C(#N)C>[CH3:23][S:24]([N:1]([C:2]1[CH:15]=[CH:14][C:13]2[C:4](=[C:5]([C:16]3[CH:21]=[CH:20][C:19]([CH3:22])=[CH:18][CH:17]=3)[C:6]3[C:11]([N:12]=2)=[CH:10][CH:9]=[CH:8][CH:7]=3)[CH:3]=1)[S:24]([CH3:23])(=[O:26])=[O:25])(=[O:26])=[O:25]

Participants

5

Reactant 3

HCID 31297Methanesulfonyl chlorideHCID 136165Diazabicyclo(2.2.2)octaneHCID 18940217HCID 18940217, compound2×

Product 1

HCID 18940224HCID 18940224, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
20 °C

Procedure

5.68 pbw of 2-amino-9-(4-methylphenyl)acridine (compound 12d) were dissolved with 20.3 pbw of methanesulfonyl chloride and 22.4 pbw of diazabicyclo[2.2.2]octane in 120 pbv of acetonitrile and the solution heated for 2 hours under reflux. After cooling to 20° C., filtration was carried out and the red filtrate added dropwise to 1000 pbv of 0.5% strength ammonia solution. After standing overnight, the precipitate was filtered off by suction and crystallized from 135 pbv of ethanol. Yield: 1.76 pbw (20% of theory), light yellow needles. Mp.: 217°-219° C.

Workup

  1. temperaturethe solution heated for 2 hours
  2. temperatureunder reflux
  3. filtrationfiltration
  4. additionthe red filtrate added dropwise to 1000 pbv of 0.5% strength ammonia solution
  5. filtrationthe precipitate was filtered off by suction
  6. customcrystallized from 135 pbv of ethanol

Sources & evidence

ORD record
ord-bbb9b5d1220b4263bb77e16a751e72f6
Source dataset
uspto-grants-1998_11
Patent number
US05834157

Reaction notes

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