Ammonia → HCID 58526512, compound

HRID 1190242Notes

Reaction equation

HRID 1190242 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH:8]=[C:9]([Br:11])[CH:10]=1)[C:5](Cl)=O.[Cl:12][C:13]1[CH:14]=[C:15]([C:25]#[N:26])[CH:16]=[C:17]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[CH:18]=1.[Sb](Cl)(Cl)(Cl)(Cl)Cl.[NH3:33]>ClC1C=CC=CC=1>[Cl:12][C:13]1[CH:14]=[C:15]([C:25]2[N:26]=[C:25]([C:15]3[CH:16]=[C:17]([C:19]4[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=4)[CH:18]=[C:13]([Cl:12])[CH:14]=3)[N:33]=[C:5]([C:4]3[CH:3]=[C:2]([Br:1])[CH:10]=[C:9]([Br:11])[CH:8]=3)[N:26]=2)[CH:16]=[C:17]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[CH:18]=1

Participants

6

Reactant 4

HCID 222AmmoniaHCID 24294Antimony pentachlorideHCID 134505263,5-Dibromobenzoyl chlorideHCID 463146615-Chloro[1,1′-biphenyl]-3-carbonitrile

Product 1

HCID 58526512HCID 58526512, compound

Reagents, catalysts & solvents 1

HCID 7964ChlorobenzeneSolvent

Conditions

Temperature
0 °C

Procedure

In a stream of argon, a 300 ml three-necked flask equipped with a reflux condenser was charged with 3,5-dibromobenzoyl chloride (10.5 g) and 5-chlorobiphenyl-3-carbonitrile (15.0 g), and then chlorobenzene (100 mL) was added to the content. The thus-obtained solution was cooled to 0° C., and antimony pentachloride (10.5 g) was dropwise added thereto. The resultant mixture was stirred at room temperature for 20 minutes and then refluxed at 100° C. for 2.5 hours. The thus-obtained red-colored solution was cooled to −20° C., and an aqueous 28% ammonia solution (50 mL) was added to obtain a milky white liquid suspension. The suspension was stirred at room temperature for 3 hours, and then, gradually heated to 140° C. in an oil bath to distill away the organic solvent (80 mL) and water (28 mL). Chlorobenzene (100 mL×3) was added to the solution, and then the solution was filtered at 130° C. The filtrate was left to stand at room temperature, and then methanol (300 mL) was added thereto. The thus-obtained solid precipitate was collected by filtration, and washed with methanol twice (50 mL×2) and dried. Thus, 2.21 g of 4,6-bis(5-chlorobiphenyl-3-yl)-2-(3,5-dibromophenyl)-1,3,5-triazine was obtained as a white powder (yield: 9%).

Workup

  1. customIn a stream of argon, a 300 ml three-necked flask equipped with a reflux condenser
  2. temperaturerefluxed at 100° C. for 2.5 hours
  3. temperatureThe thus-obtained red-colored solution was cooled to −20° C.
  4. customto obtain a milky white liquid suspension
  5. temperaturegradually heated to 140° C. in an oil bath
  6. distillationto distill away the organic solvent (80 mL) and water (28 mL)
  7. additionChlorobenzene (100 mL×3) was added to the solution
  8. filtrationthe solution was filtered at 130° C
  9. waitThe filtrate was left
  10. customto stand at room temperature
  11. additionmethanol (300 mL) was added
  12. filtrationThe thus-obtained solid precipitate was collected by filtration
  13. washwashed with methanol twice (50 mL×2)
  14. customdried

Sources & evidence

ORD record
ord-93e34068b9bf41878b5558575df47d32
Source dataset
uspto-grants-2014_03
Patent number
US08674091B2

Reaction notes

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