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

HRID 60233ノート

反応式

HRID 60233 の反応式
[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

参加物

5

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 6344Dichloromethane溶媒HCID 24813Phosphorus oxychloride溶媒

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-c506f744ec6549f39ec81b329f5fd21b
出典データセット
uspto-grants-2016_09
特許番号
US09440976B2

反応ノート

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