Phosphorus pentachloride → HCID 58365104, 화합물

HRID 60225노트

반응식

HRID 60225 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]([F: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]>ClC1C=CC=CC=1.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]([F: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 58364995HCID 58364995, 화합물

생성물 1

HCID 58365104HCID 58365104, 화합물수율 65%

시약·촉매·용매 2

HCID 6344Dichloromethane용매HCID 7964Chlorobenzene용매

실험 절차

A solution of 9-benzenesulfonyl-3-fluoro-5-hydroxy-9H-dipyrido[2,3-b;4′,3′-d]pyrrole-6-carbonitrile (500 mg, 1.36 mmol) and phosphorus pentachloride (708 mg, 3.4 mmol) in chlorobenzene (1.5 mL) was heated at 110° C. for 1 hour. 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 (50 mL) and then the solution was diluted with ice/water (50 mL). The layers were separated and the aqueous layer further extracted with dichloromethane (50 mL). 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 (320 mg, 65%). 1H NMR (400 MHz, CDCl3): 9.81 (s, 1H), 8.69 (d, J=2.8 Hz, 1H), 8.50 (dd, J=7.6, 2.8 Hz, 1H), 8.24 (d, J=8.0 Hz, 2H), 7.65 (t, J=7.5 Hz, 1H), 7.53 (t, J=7.8 Hz, 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 (50 mL)
  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-e1cc1c3102d740f9b4289c4efe61e35d
출처 데이터셋
uspto-grants-2016_09
특허 번호
US09440976B2

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