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

HRID 60233노트

반응식

HRID 60233 반응식
[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

참가 물질

5

반응물 2

HCID 24819Phosphorus pentachlorideHCID 583649529-Benzenesulfonyl-3-chloro-5-hydroxy-9H-diprido[2,3-b;4',3'-d]pyrrole-6-carbonitrile

생성물 1

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

시약·촉매·용매 2

HCID 6344Dichloromethane용매HCID 24813Phosphorus oxychloride용매

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-c506f744ec6549f39ec81b329f5fd21b
출처 데이터셋
uspto-grants-2016_09
특허 번호
US09440976B2

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