Iodine → 2-Chloro-4,6-diphenyl-1,3,5-triazine

HRID 1863198Notes

Reaction equation

HRID 1863198 reaction equation
[Mg].II.Br[C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1.[N:11]1[C:18](Cl)=[N:17][C:15](Cl)=[N:14][C:12]=1[Cl:13]>CCOCC.C1C=CC=CC=1>[Cl:13][C:12]1[N:14]=[C:15]([C:5]2[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=2)[N:17]=[C:18]([C:5]2[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=2)[N:11]=1

Participants

7

Reactant 4

HCID 807IodineHCID 7954Cyanuric chlorideHCID 7961BromobenzeneHCID 5462224Magnesium

Product 1

HCID 196982-Chloro-4,6-diphenyl-1,3,5-triazineYield 134.2%

Reagents, catalysts & solvents 2

HCID 241BenzeneSolventHCID 3283Diethyl EtherSolvent2×

Procedure

The procedure used was based on the method of Jones et al, AD 229453, Sept. 1959. A stirred mixture of magnesium turnings (24.3 g, 0.935 mol) and a crystal of iodine in ether (150 ml), was added a solution of bromobenzene (155.3 g, 0.985 mol) in ether (100 ml) under a nitrogen atmosphere over a period of 3.75 hr at such a rate as to maintain a gentle reflux. Thereafter, the mixture was refluxed for 2.5 hr. The Grignard reagent thus prepared was then cooled and transferred to an addition funnel and added with stirring to a solution of cyanuric chloride (70 g, 0.38 mol) in benzene (500 ml) at 4°-15° C. (ice bath cooling) over a period of 1.25 hr. After stirring overnight the mixture was refluxed for 4 hr, cooled, and filtered. The filtrate was evaporated to dryness using a Rinco evaporator yielding 136.5 g of crude product mixture. This mixture was distilled in vacuo at 0.007 mm. The desired product, bp 140°-152° C., 63.5 g(62% yield), was crystallized three times from heptane yielding pure 2-chloro-4,6-diphenyl-s-triazine, 46.1 g (45% yield), mp 136°-138° C.

Workup

  1. temperatureto maintain a gentle reflux
  2. temperatureThereafter, the mixture was refluxed for 2.5 hr
  3. temperaturewas then cooled
  4. customtransferred to an addition funnel
  5. additionadded
  6. temperature(ice bath cooling) over a period of 1.25 hr
  7. temperaturewas refluxed for 4 hr
  8. temperaturecooled
  9. filtrationfiltered
  10. customThe filtrate was evaporated to dryness
  11. customa Rinco evaporator

Sources & evidence

ORD record
ord-c7be77463f5b4da9ab1d69c7701f2edd
Source dataset
uspto-grants-1979_09
Patent number
US04168287

Reaction notes

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