Carbon Tetrachloride → 4,7-Diphenyl-2,9-bis(trichloromethyl)-1,10-phenanthroline

HRID 622652Notes

Reaction equation

HRID 622652 reaction equation
C[C:2]1[CH:15]=[C:14]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[C:13]2[C:4](=[C:5]3[C:10](=[CH:11][CH:12]=2)[C:9]([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)=[CH:8][C:7](C)=[N:6]3)[N:3]=1.ClN1C(=O)CCC1=O.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1.[C:55]([Cl:59])([Cl:58])([Cl:57])Cl.[CH:60]([Cl:63])([Cl:62])[Cl:61]>>[Cl:61][C:60]([Cl:63])([Cl:62])[C:7]1[CH:8]=[C:9]([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[C:10]2[C:5](=[C:4]3[C:13](=[CH:12][CH:11]=2)[C:14]([C:16]2[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=2)=[CH:15][C:2]([C:55]([Cl:59])([Cl:58])[Cl:57])=[N:3]3)[N:6]=1

Participants

6

Reactant 5

HCID 5943Carbon TetrachlorideHCID 6212ChloroformHCID 7187Benzoyl PeroxideHCID 31398ChlorosuccinimideHCID 651491,10-Phenanthroline, 2,9-dimethyl-4,7-diphenyl-

Product 1

HCID 149578744,7-Diphenyl-2,9-bis(trichloromethyl)-1,10-phenanthroline

Procedure

A mixture composed of 2,9,-dimethyl-4,7-diphenyl-1,10-phenanthroline (4.0 g, 0.011 mole), N-chlorosuccinimide (9.0 g, 0.067 mole), benzoyl peroxide (0.011 g) and 96 ml carbon tetrachloride was stirred for 6 hr in an oil bath at 90°. After standing overnight at 4° C., crystals of succinimide were removed by filtration. The solvent was removed from the filtrate by vacuum evaporation to produce a light yellow solid which was then dissolved in chloroform. The organic layer was washed with saturated sodium carbonate solution and dried over anhydrous magnesium sulfate. Removal of solvent by vacuum evaporation yielded the white solid product. Yield=6.1 g (97%). Mp=286°-289°. IR 3020-3080, 1620, 1570, 1550, 1490, 1445, 1405, 1360, 1220, 1040, 930, 895, 835, 800, 780, 760, 735, 700, 620 cm-1. 60 MHz proton NMR in CDCl3 δ7.55 singlet (10 protons), δ8.05 singlet (2 protons), δ8.3 singlet (2 protons).

Workup

  1. waitAfter standing overnight at 4° C.
  2. customcrystals of succinimide were removed by filtration
  3. customThe solvent was removed from the filtrate by vacuum evaporation
  4. customto produce a light yellow solid which
  5. washThe organic layer was washed with saturated sodium carbonate solution
  6. dry with materialdried over anhydrous magnesium sulfate
  7. customRemoval of solvent
  8. customby vacuum evaporation
  9. customyielded the white solid product

Sources & evidence

ORD record
ord-9e60bcd950a04e8c973675bbbd9c58e7
Source dataset
uspto-grants-1988_09
Patent number
US04772563

Reaction notes

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