Hydrochloric Acid → HCID 135845402, compound

HRID 362686Notes

Reaction equation

HRID 362686 reaction equation
[Cl-].[Cl-].[Cl-].[Al+3].[C:5]1([CH3:21])[CH:10]=[C:9]([CH3:11])[CH:8]=[C:7]([CH3:12])[C:6]=1[C:13]1[N:18]=[C:17](Cl)[N:16]=[C:15](Cl)[N:14]=1.[C:22]1([CH:29]=[CH:28][CH:27]=[C:25]([OH:26])[CH:24]=1)[OH:23].Cl>S1(CCCC1)(=O)=O>[C:5]1([CH3:21])[CH:10]=[C:9]([CH3:11])[CH:8]=[C:7]([CH3:12])[C:6]=1[C:13]1[N:18]=[C:17]([C:27]2[CH:28]=[CH:29][C:22]([OH:23])=[CH:24][C:25]=2[OH:26])[N:16]=[C:15]([C:27]2[CH:28]=[CH:29][C:22]([OH:23])=[CH:24][C:25]=2[OH:26])[N:14]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 5054ResorcinolHCID 6451240Aluminum(III) ChlorideHCID 54528417HCID 54528417, compound

Product 1

HCID 135845402HCID 135845402, compoundYield 84.6%

Reagents, catalysts & solvents 1

HCID 31347SulfolaneSolvent2×

Procedure

148.7 g (1.21 mol) of anhydrous aluminium trichloride (purity 98%) are added with stirring to a suspension of 130.0 g (0.485 mol) of 2-mesityl-4,6-dichloro-1,3,5-triazine (i) in 300 ml of petroleum ether with a boiling range of 110°-140° C. and 385 ml of sulfolane. During this addition, the mixture warms to 45° C. A solution of 133.5 e (1.21 mol) of resorcinol (purity 98%) in 155 ml of sulfolane is added to the mixture over the course of 45 minutes. The mixture is warmed at 80°-85° C. for 5 hours 30 minutes with evolution of HCl. The upper phase (petroleum ether) is removed, and the lower, viscous phase is transferred while still hot into a stirred mixture of 2.11 of methanol and 2.11 of water. After the mixture has been stirred for 14 hours, the solid is filtered off, stirred in 2.2 l of 1 molar HCl for 1 hour and re-filtered. The filter cake is suspended in 1000 ml of water, stirred for 30 minutes and re-filtered. This operation is repeated twice. The filter cake is dried for 24 hours at 80° C. and a pressure of 60 mmHg (8000 Pa), giving 170.5 g of the title product (ii) of the formula ##STR62## of m.p. 230°-234° C.

Workup

  1. additionDuring this addition
  2. customwarms to 45° C
  3. customThe upper phase (petroleum ether) is removed
  4. additionstill hot into a stirred mixture of 2.11 of methanol and 2.11 of water
  5. filtrationthe solid is filtered off
  6. stirringstirred in 2.2 l of 1 molar HCl for 1 hour
  7. filtrationre-filtered
  8. stirringstirred for 30 minutes
  9. filtrationre-filtered
  10. customThe filter cake is dried for 24 hours at 80° C.

Sources & evidence

ORD record
ord-67411f5d4f5c42c18b5e51bd70ed07ff
Source dataset
uspto-grants-1999_02
Patent number
US05869588

Reaction notes

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