Chlorosuccinimide → HCID 20363323, compound

HRID 1730444Notes

Reaction equation

HRID 1730444 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([Cl:8])[C:3]=1[C:9]1[NH:10][C:11]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)=[C:12]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[N:13]=1.[Cl:26]N1C(=O)CCC1=O>C(Cl)(Cl)(Cl)Cl>[Cl:26][N:13]1[C:12]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)=[C:11]([C:20]2[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=2)[N:10]=[C:9]1[C:3]1[C:4]([Cl:8])=[CH:5][CH:6]=[CH:7][C:2]=1[Cl:1]

Participants

4

Reactant 2

HCID 31398ChlorosuccinimideHCID 1933876HCID 1933876, compound

Product 1

HCID 20363323HCID 20363323, compound

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

A mixture of 14.60 g. (0.04 mole) of the 2-(2',6'-dichlorophenyl)-4,5-diphenylimidazole, 5.34 g. (0.04 mole) of N-chlorosuccinimide, and 400 ml of carbon tetrachloride was heated at reflux temperature for 2 hours. The solution was cooled, filtered, and thefiltrate concentrated under vacuum. The resulting solid-oil mixture was triturated with 1-chlorobutane to give a residue of 16.68 g., m.p. 120°-140° C. (broad). The compound proved difficult to recrystallize from common solvents and only acetonitrile and nitromethane afforded reasonable recovery of crystals; from the latter solvents the crystals formed as large chunky aggregates. The best fraction 0.7664 g. has m.p. 125°-127° C.; an IR spectrum showed no NH absorption and a very strong 1620 cm-1 band.

Workup

  1. additionA mixture of 14.60 g
  2. temperatureat reflux temperature for 2 hours
  3. temperatureThe solution was cooled
  4. filtrationfiltered
  5. concentrationthefiltrate concentrated under vacuum
  6. customThe resulting solid-oil mixture was triturated with 1-chlorobutane
  7. customto give a residue of 16.68 g
  8. customto recrystallize from common solvents and only acetonitrile and nitromethane afforded reasonable recovery of crystals
  9. customfrom the latter solvents the crystals formed as large chunky aggregates
  10. customno NH absorption

Sources & evidence

ORD record
ord-f63d2d4eb7894d1b9f4e25aa11ab69d3
Source dataset
uspto-grants-1976_11
Patent number
US03992450

Reaction notes

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