Hydrochloric Acid → 2-Chloro-4,6-bis(4-methoxyphenyl)-1,3,5-triazine

HRID 232895Notes

Reaction equation

HRID 232895 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([Mg]Br)=[CH:5][CH:4]=1.[Mg].Br[C:13]1[CH:18]=[CH:17][C:16]([O:19][CH3:20])=[CH:15][CH:14]=1.[N:21]1[C:28](Cl)=[N:27][C:25](Cl)=[N:24][C:22]=1[Cl:23].Cl>C1COCC1>[Cl:23][C:22]1[N:24]=[C:25]([C:6]2[CH:7]=[CH:8][C:3]([O:2][CH3:1])=[CH:4][CH:5]=2)[N:27]=[C:28]([C:13]2[CH:18]=[CH:17][C:16]([O:19][CH3:20])=[CH:15][CH:14]=2)[N:21]=1

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 77304-BromoanisoleHCID 7954Cyanuric chlorideHCID 5462224MagnesiumHCID 178491912HCID 178491912, compound

Product 1

HCID 190861842-Chloro-4,6-bis(4-methoxyphenyl)-1,3,5-triazine

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A Grignard solution of p-methoxyphenylmagnesium bromide (prepared from 12.2 g (0.05 mol) of magnesium and 93.5 g (0.5 mol) of p-bromoanisole in 130 ml of anhydrous THF) is added to a solution of 31.3 g (0.17 mol) of cyanuric chloride in 100 ml of THF over a period of 1.5 hours while maintaining the temperature in the range from 0° to 20° C. After addition is complete, the mixture is stirred at room temperature for 1.5 hours and then poured into 150 ml of 12% hydrogen chloride solution in an ice-bath. The beige suspension is filtered off, washed neutral with water and then washed with methanol. The crude product is recrystallized from 350 ml of toluene to give the compound of the formula ##STR21##

Workup

  1. temperaturewhile maintaining the temperature in the range from 0° to 20° C
  2. additionAfter addition
  3. filtrationThe beige suspension is filtered off
  4. washwashed neutral with water
  5. washwashed with methanol
  6. customThe crude product is recrystallized from 350 ml of toluene
  7. customto give the compound of the formula

Sources & evidence

ORD record
ord-ebf64fc2288843c88f7a6308cbb70e4c
Source dataset
uspto-grants-1997_01
Patent number
US05591850

Reaction notes

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