Chlorosulfonic acid → HCID 59180464, compound

HRID 1925740Notes

Reaction equation

HRID 1925740 reaction equation
[C:1]1([CH3:12])[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[N:7]1[CH2:11][CH2:10][CH2:9][CH2:8]1.Cl[S:14]([OH:17])(=[O:16])=[O:15]>ClCCl>[CH3:12][C:1]1[CH:6]=[C:5]([S:14]([OH:17])(=[O:16])=[O:15])[CH:4]=[CH:3][C:2]=1[N:7]1[CH2:11][CH2:10][CH2:9][CH2:8]1

Participants

4

Reactant 2

HCID 24638Chlorosulfonic acidHCID 142531N-(2-Methylphenyl)pyrrolidine

Product 1

HCID 59180464HCID 59180464, compoundYield 96.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a cooled (0° C.) solution of 119 (1.24 g; 7.7 mmol) in anhydrous dichloromethane (38 mL) was added chlorosulfonic acid (0.61 mL; 9.24 mmol) dropwise (1 mL/minutes). The reaction mixture w as allowed to gradually warm to room temperature while stirring overnight. The reaction mixture was concentrated under reduced pressure. The resulting oil w as taken up in diisopropyl ether (10 mL) and aqueous hydrochloric acid (0.5 mL; 2N) then stirred vigorously at room temperature for 2 hours. The organic phase was separated and concentrated under reduced pressure to yield the desired compound as an amber oil (1.8 g).

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. stirringaqueous hydrochloric acid (0.5 mL; 2N) then stirred vigorously at room temperature for 2 hours
  3. customThe organic phase was separated
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-2b8d1782863e4dd78ecd46edd2f54e78
Source dataset
uspto-grants-2012_05
Patent number
US08178699B2

Reaction notes

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