Diphenyl Ether → HCID 21250019, compound

HRID 1531690Notes

Reaction equation

HRID 1531690 reaction equation
C[O:2][C:3]([C:5]([S:18]([CH2:21][C:22]([F:25])([F:24])[F:23])(=[O:20])=[O:19])=[CH:6][NH:7][C:8]1[CH:9]=[CH:10][CH:11]=[C:12]2[C:17]=1[N:16]=[CH:15][CH:14]=[CH:13]2)=O.C1(OC2C=CC=CC=2)C=CC=CC=1>CCCCCC>[F:25][C:22]([F:23])([F:24])[CH2:21][S:18]([CH:5]1[C:3](=[O:2])[C:9]2[C:8](=[C:17]3[C:12](=[CH:11][CH:10]=2)[CH:13]=[CH:14][CH:15]=[N:16]3)[N:7]=[CH:6]1)(=[O:19])=[O:20]

Participants

4

Reactant 2

HCID 7583Diphenyl EtherHCID 69951340HCID 69951340, compound

Product 1

HCID 21250019HCID 21250019, compound

Reagents, catalysts & solvents 1

HCID 8058HexaneSolvent

Conditions

Temperature
260 °C

Procedure

8-[2-Methoxycarbonyl-2-(2,2,2-trifluoroethylsulfonyl)-ethenylamino]quinoline (4 g) was added to diphenyl ether (100 ml) with stirring at 260° C., and stirring was continued for 2 hours. The mixture was allowed to cool to ambient temperature and hexane (100 ml) was added. The mixture was filtered, and the residue purified by flash chromatography on silica using increasingly polar mixtures of methanol and chloroform as eluant. The product so obtained was recrystallised from acetic acid to give 3-(2,2,2-trifluoroethyl-sulfonyl)-4-oxo-3,4-dihydro-1,10-phenanthroline, mp 272-274° C.

Workup

  1. stirringstirring
  2. temperatureto cool to ambient temperature
  3. filtrationThe mixture was filtered
  4. customthe residue purified by flash chromatography on silica using
  5. temperatureincreasingly polar mixtures of methanol and chloroform as eluant
  6. customThe product so obtained
  7. customwas recrystallised from acetic acid

Sources & evidence

ORD record
ord-72a7e2577b0c4eb5bac6ad22411ea7bf
Source dataset
uspto-grants-2001_03
Patent number
US06200974B1

Reaction notes

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