Phosphorus pentachloride → 9-Benzenesulfonyl-3,5-dichloro-9H-dipyrido[2,3-b;4',3'-d]pyrrole-6-carbonitrile

HRID 60233Notes

Reaction equation

HRID 60233 reaction equation
[C:1]1([S:7]([N:10]2[C:14]3[CH:15]=[N:16][C:17]([C:20]#[N:21])=[C:18](O)[C:13]=3[C:12]3[CH:22]=[C:23]([Cl:26])[CH:24]=[N:25][C:11]2=3)(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.P(Cl)(Cl)(Cl)(Cl)[Cl:28]>P(Cl)(Cl)(Cl)=O.ClCCl>[C:1]1([S:7]([N:10]2[C:14]3[CH:15]=[N:16][C:17]([C:20]#[N:21])=[C:18]([Cl:28])[C:13]=3[C:12]3[CH:22]=[C:23]([Cl:26])[CH:24]=[N:25][C:11]2=3)(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

5

Reactant 2

HCID 24819Phosphorus pentachlorideHCID 58364952HCID 58364952, compound

Product 1

HCID 583650319-Benzenesulfonyl-3,5-dichloro-9H-dipyrido[2,3-b;4',3'-d]pyrrole-6-carbonitrileYield 59%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 24813Phosphorus oxychlorideSolvent

Procedure

A solution of 9-benzenesulfonyl-3-chloro-5-hydroxy-9H-dipyrido[2,3-b;4′,3′-d]pyrrole-6-carbonitrile (1.9 g, 4.94 mmol) and phosphorus pentachloride (3.1 g, 14.8 mmol) in phosphorus oxychloride (8 mL) was heated at 105° C. for 2 hours. The reaction mixture was cooled to ambient temperature and then the solvent removed in-vacuo to afford a residue. The resultant residue was dissolved in dichloromethane (300 mL) and then the solution was diluted with ice/water (300 mL). The layers were separated and the aqueous layer further extracted with dichloromethane. The combined organic layer was washed with brine, dried (Na2SO4), filtered and evaporated. The resultant residue was triturated with diethyl ether and dried to afford the title compound as a tan solid (1.17 g, 59%). 1H NMR (400 MHz, CDCl3): 9.81 (s, 1H), 8.77 (d, J=2.4 Hz, 1H), 8.75 (d, J=2.4 Hz, 1H), 8.26-8.22 (m, 2H), 7.66-7.66 (m, 1H), 7.53-7.53 (m, 2H).

Workup

  1. customthe solvent removed in-vacuo
  2. customto afford a residue
  3. customThe layers were separated
  4. extractionthe aqueous layer further extracted with dichloromethane
  5. washThe combined organic layer was washed with brine
  6. dry with materialdried (Na2SO4)
  7. filtrationfiltered
  8. customevaporated
  9. customThe resultant residue was triturated with diethyl ether
  10. customdried

Sources & evidence

ORD record
ord-c506f744ec6549f39ec81b329f5fd21b
Source dataset
uspto-grants-2016_09
Patent number
US09440976B2

Reaction notes

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