Ammonia → HCID 90401467, compound

HRID 1773054Notes

Reaction equation

HRID 1773054 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][CH:10]=1)[C:5](Cl)=O.[C:11]1([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[CH:16]=[CH:15][C:14]([C:17]#[N:18])=[CH:13][CH:12]=1.[Sb](Cl)(Cl)(Cl)(Cl)Cl.[NH3:31]>ClC1C=CC=CC=1>[C:11]1([C:19]2[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=2)[CH:12]=[CH:13][C:14]([C:17]2[N:18]=[C:17]([C:14]3[CH:15]=[CH:16][C:11]([C:19]4[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=4)=[CH:12][CH:13]=3)[N:31]=[C:5]([C:4]3[CH:8]=[CH:9][CH:10]=[C:2]([Br:1])[CH:3]=3)[N:18]=2)=[CH:15][CH:16]=1

Participants

6

Reactant 4

HCID 222AmmoniaHCID 18021(1,1'-Biphenyl)-4-carbonitrileHCID 24294Antimony pentachlorideHCID 74377Benzoyl chloride, 3-bromo-

Product 1

HCID 90401467HCID 90401467, compound

Reagents, catalysts & solvents 1

HCID 7964ChlorobenzeneSolvent

Conditions

Temperature
0 °C

Procedure

1.9 g of 3-bromobenzoic acid chloride and 3.10 g of 4-biphenylcarbonitrile were dissolved in 50 mL of chlorobenzene in a stream of argon. The thus-obtained solution was cooled to 0° C., and then 2.59 g of antimony pentachloride was dropwise added therein. The mixture was stirred at room temperature for one hour, and then heated at 100° C. for 2 hours. The reaction mixture was left to be cooled to room temperature, and further to −20° C. Aqueous 28% ammonia was added therein to give a white precipitate. The white precipitate-containing suspension was stirred overnight at room temperature. The thus-deposited solid was collected by filtration and washed with methanol. The thus-washed solid was dried and then extracted by a Soxhlet's extractor using chloroform as extraction solvent to give 2.00 g of 2,4-di(4-biphenylyl)-6-(3-bromophenyl)-1,3,5-triazine as a white powder (yield, 43%).

Workup

  1. temperatureheated at 100° C. for 2 hours
  2. waitThe reaction mixture was left
  3. temperatureto be cooled to room temperature
  4. customfurther to −20° C
  5. customto give a white precipitate
  6. stirringThe white precipitate-containing suspension was stirred overnight at room temperature
  7. filtrationThe thus-deposited solid was collected by filtration
  8. washwashed with methanol
  9. customThe thus-washed solid was dried
  10. extractionextracted by a Soxhlet's extractor
  11. extractionas extraction solvent
  12. customto give

Sources & evidence

ORD record
ord-e0dc253598c14968a8c87f4a41314b70
Source dataset
uspto-grants-2016_02
Patent number
US09252368B2

Reaction notes

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