Chlorosulfonic acid → HCID 86601723, compound

HRID 1784416Notes

Reaction equation

HRID 1784416 reaction equation
[Cl:1][S:2]([OH:5])(=O)=[O:3].[CH2:6]([O:8][C:9]1[CH:10]=[C:11]2[C:16](=[CH:17][CH:18]=1)[CH2:15][N:14]([C:19](=[O:24])[C:20]([F:23])([F:22])[F:21])[CH2:13][CH2:12]2)[CH3:7]>ClCCl>[CH2:6]([O:8][C:9]1[CH:10]=[C:11]2[C:16](=[CH:17][C:18]=1[S:2]([Cl:1])(=[O:5])=[O:3])[CH2:15][N:14]([C:19](=[O:24])[C:20]([F:21])([F:22])[F:23])[CH2:13][CH2:12]2)[CH3:7]

Participants

4

Reactant 2

HCID 24638Chlorosulfonic acidHCID 86601722HCID 86601722, compound

Product 1

HCID 86601723HCID 86601723, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of chlorosulfonic acid (0.48 mL) in dichloromethane (5 mL) at 0° C. was added dropwise a solution of 1-(6-ethoxy-3,4-dihydro-1H-isoquinolin-2-yl)-2,2,2-trifluoro-ethanone (0.39 g, 1.43 mmol). The mixture was stirred at room temperature overnight before partitioning between water and dichloromethane. The organic layer was removed, dried over sodium sulfate, filtered and evaporated to dryness yielding the subtitled compound as a clear oil (0.34 g). 1H NMR δ (CDCl3) 1.46-1.63 (3H, t), 2.95-3.06 (2H, m), 3.80-3.95 (2H, m), 4.18-4.32 (2H, m), 4.69-4.80 (2H, d), 6.84-6.93 (1H, d), 7.70-7.79 (1H, d).

Workup

  1. custombefore partitioning between water and dichloromethane
  2. customThe organic layer was removed
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered
  5. customevaporated to dryness

Sources & evidence

ORD record
ord-92285f3590cb4cb1a48b6f87416fb2dd
Source dataset
uspto-grants-2009_03
Patent number
US07504392B2

Reaction notes

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