Chlorosulfonic acid → 2,3-dihydro-2-trifluoroacetyl-1H-Benz[de]isoquinoline-6-sulfonyl chloride

HRID 1068560Notes

Reaction equation

HRID 1068560 reaction equation
[Cl:1][S:2]([OH:5])(=O)=[O:3].[F:6][C:7]([F:24])([F:23])[C:8]([N:10]1[CH2:19][C:18]2[CH:20]=[CH:21][CH:22]=[C:16]3[C:17]=2[C:12](=[CH:13][CH:14]=[CH:15]3)[CH2:11]1)=[O:9]>C(Cl)(Cl)Cl>[F:24][C:7]([F:6])([F:23])[C:8]([N:10]1[CH2:11][C:12]2[CH:13]=[CH:14][C:15]([S:2]([Cl:1])(=[O:5])=[O:3])=[C:16]3[C:17]=2[C:18](=[CH:20][CH:21]=[CH:22]3)[CH2:19]1)=[O:9]

Participants

4

Reactant 2

HCID 24638Chlorosulfonic acidHCID 211895902,3-Dihydro-2-trifluoroacetyl-1h-benz[de]isoquinoline

Product 1

HCID 211896072,3-dihydro-2-trifluoroacetyl-1H-Benz[de]isoquinoline-6-sulfonyl chloride

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Conditions

Temperature
0 °C

Procedure

Chlorosulfonic acid (40 mmol) is added dropwise to a cold (0° C.) solution of 2,3-dihydro-2-trifluoroacetyl-1H-Benz[de]isoquinoline (8 mmol) in chloroform (800 mL). The resulting solution is stirred at 0° C. for 30 minutes. The cold bath is then removed and the solution is stirred at room temperature for 1 hour then cautiously poured into ice-water. The organic layer is separated, dried over magnesium sulfate and concentrated to afford the title compound. The crude product can be purified by recrystallization or chromatography.

Workup

  1. customThe cold bath is then removed
  2. stirringthe solution is stirred at room temperature for 1 hour
  3. additionthen cautiously poured into ice-water
  4. customThe organic layer is separated
  5. dry with materialdried over magnesium sulfate
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-4ccaca7ba03b44a3a8d63d5648e66052
Source dataset
uspto-grants-2001_06
Patent number
US06251890B1

Reaction notes

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