Thionyl Chloride → 2-chloro-N-{3-[4-(chloromethyl)phenyl]pyrazin-2-yl}benzenesulfonamide

HRID 2401028Notes

Reaction equation

HRID 2401028 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[S:8]([NH:11][C:12]1[C:17]([C:18]2[CH:23]=[CH:22][C:21]([CH2:24]O)=[CH:20][CH:19]=2)=[N:16][CH:15]=[CH:14][N:13]=1)(=[O:10])=[O:9].S(Cl)([Cl:28])=O>ClCCl>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[S:8]([NH:11][C:12]1[C:17]([C:18]2[CH:23]=[CH:22][C:21]([CH2:24][Cl:28])=[CH:20][CH:19]=2)=[N:16][CH:15]=[CH:14][N:13]=1)(=[O:10])=[O:9]

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 57586070HCID 57586070, compound

Product 1

HCID 574442542-chloro-N-{3-[4-(chloromethyl)phenyl]pyrazin-2-yl}benzenesulfonamideYield 95%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

2-chloro-N-{3-[4-(hydroxymethyl)phenyl]pyrazin-2-yl}benzene sulfonamide (3.15 g; 8.4 mmol; 1.00 eq.) was dissolved in dichloromethane (80 mL) and thionyl chloride (8.5 mL, 117 mmol, 14 eq.) was added dropwise. The reaction mixture was stirred overnight. The reaction mixture was poured carefully into ice/water (200 mL) and stirred until clear layers were formed. The mixture was separated and the organic layer was dried over MgSO4 and evaporated down to give the crude solid which was recrystallised in AcOEt/cyclohexane to give the pure 2-chloro-N-{3-[4-(chloromethyl)phenyl]pyrazin-2-yl}benzenesulfonamide as a white solid (3.02 g, 95% yield, 99% HPLC purity).

Workup

  1. stirringstirred until clear layers
  2. customwere formed
  3. customThe mixture was separated
  4. dry with materialthe organic layer was dried over MgSO4
  5. customevaporated down
  6. customto give the crude solid which
  7. customwas recrystallised in AcOEt/cyclohexane

Sources & evidence

ORD record
ord-a84b61c6dfeb4a52ad621876c2630327
Source dataset
uspto-grants-2014_08
Patent number
US08796280B2

Reaction notes

Loading…