Chlorosulfonic acid → HCID 86713352, compound

HRID 928041Notes

Reaction equation

HRID 928041 reaction equation
[Cl:1][S:2]([OH:5])(=O)=[O:3].[CH2:6]([N:8]1[CH2:13][CH2:12][N:11]([CH2:14][C:15]2[CH:20]=[CH:19][CH:18]=[C:17]([F:21])[CH:16]=2)[C:10](=[O:22])[CH2:9]1)[CH3:7]>>[CH2:6]([N:8]1[CH2:13][CH2:12][N:11]([CH2:14][C:15]2[CH:16]=[C:17]([F:21])[CH:18]=[CH:19][C:20]=2[S:2]([Cl:1])(=[O:5])=[O:3])[C:10](=[O:22])[CH2:9]1)[CH3:7]

Participants

3

Reactant 2

HCID 24638Chlorosulfonic acidHCID 70984334HCID 70984334, compound2×

Product 1

HCID 86713352HCID 86713352, compound

Procedure

Chlorosulphonic acid (2 mL) was added to 4-ethyl-1-(3-fluorobenzyl)-piperazin-2-one (Intermediate 175, 0.59 g) with stirring and cooling in ice. The cooling was removed and the solution was stirred at room temperature for 4 hours before being carefully added to a mixture of ethyl acetate, ice and sodium bicarbonate. The organic layer was dried (Na2SO4) and filtered and the filtrate was concentrated in vacuo to give 2-(4-ethyl-2-oxopiperazin-1-ylmethyl)-4-fluoro-benzenesulfonyl chloride (0.37 g) as a colourless gum.

Workup

  1. temperaturecooling in ice
  2. customThe cooling was removed
  3. stirringthe solution was stirred at room temperature for 4 hours
  4. additionbefore being carefully added to a mixture of ethyl acetate, ice and sodium bicarbonate
  5. dry with materialThe organic layer was dried (Na2SO4)
  6. filtrationfiltered
  7. concentrationthe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-ce48f1ca96b044b69547ae318d7df38d
Source dataset
uspto-grants-2016_03
Patent number
US09290472B2

Reaction notes

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