Hydrochloric Acid → 2,4-Dichloro-6-phenyl-1,3,5-triazine

HRID 1755700Notes

Reaction equation

HRID 1755700 reaction equation
II.Br[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.[N:10]1[C:17]([Cl:18])=[N:16][C:14](Cl)=[N:13][C:11]=1[Cl:12].Cl>C1COCC1.C1(C)C=CC=CC=1>[Cl:12][C:11]1[N:10]=[C:17]([Cl:18])[N:16]=[C:14]([C:4]2[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=2)[N:13]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 807IodineHCID 7954Cyanuric chlorideHCID 7961Bromobenzene

Product 1

HCID 155492,4-Dichloro-6-phenyl-1,3,5-triazineYield 61%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 8028TetrahydrofuranSolvent3×

Conditions

Temperature
25 °C

Procedure

7.80 g (0.32 mol) of iodine-activated magnesium turnings in 20 ml of anhydrous THF are heated briefly to 60° C. Then 47.1 g (0.30 mol) of bromobenzene and 80 ml of THF are added dropwise over 30 min and the mixture is heated for 1.5 hours to 65° C. After cooling, the Grignard solution is added over 1 hour to a mixture of 51.6 g (0.28 mol) of cyanuric chloride and 140 ml of THF, while keeping the temperature of the mixture in the range from 10° to 20° C. When the addition is complete, the mixture is stirred at for 3 hours at 25° C. The mixture is then diluted with 280 ml of toluene, the resultant suspension is poured into 300 g of 12% aqueous HCl, the organic phase is separated, washed with a total amount of 400 g of water and concentrated. The resultant material (melting point 117°-120° C.) is recrystallised from hexane, giving the title compound in a yield of 61%.

Workup

  1. temperaturethe mixture is heated for 1.5 hours to 65° C
  2. temperatureAfter cooling
  3. customfrom 10° to 20° C
  4. additionWhen the addition
  5. customthe organic phase is separated
  6. washwashed with a total amount of 400 g of water
  7. concentrationconcentrated
  8. customThe resultant material (melting point 117°-120° C.) is recrystallised from hexane

Sources & evidence

ORD record
ord-d4b762a83d774b57ad5c874b61977fa7
Source dataset
uspto-grants-1995_08
Patent number
US05438138

Reaction notes

Loading…