Hydrochloric Acid → HCID 135503193, compound

HRID 618605Notes

Reaction equation

HRID 618605 reaction equation
Cl[C:2]1[N:7]=[C:6](Cl)[N:5]=[C:4]([C:9]2[N:10]([CH3:14])[CH:11]=[CH:12][CH:13]=2)[N:3]=1.[C:15]1([CH:22]=[CH:21][CH:20]=[C:18]([OH:19])[CH:17]=1)[OH:16].[Cl-].[Al+3].[Cl-].[Cl-].Cl>C1(C)C(C)=CC=CC=1>[OH:16][C:15]1[CH:17]=[C:18]([OH:19])[CH:20]=[CH:21][C:22]=1[C:2]1[N:7]=[C:6]([C:20]2[CH:21]=[CH:22][C:15]([OH:16])=[CH:17][C:18]=2[OH:19])[N:5]=[C:4]([C:9]2[N:10]([CH3:14])[CH:11]=[CH:12][CH:13]=2)[N:3]=1

Participants

6

Reactant 4

HCID 313Hydrochloric Acid2×HCID 5054ResorcinolHCID 6451240Aluminum(III) ChlorideHCID 12206102HCID 12206102, compound

Product 1

HCID 135503193HCID 135503193, compoundYield 81%

Reagents, catalysts & solvents 1

HCID 7237O-XyleneSolvent

Procedure

Friedel-Crafts acylation: In a 500 ml sulfonation flask having a stirrer, dropping funnel, condenser and internal thermometer, 22.9 g (0.1 mol) of 2,4-dichloro-6-(1-methylpyrrol-2-yl)-1,3,5-triazine and 24.2 g (0.22 mol) of resorcinol are initially introduced into 200 ml of xylene (isomer mixture). At 45-50° C., 29.3 g (0.22 mol) of aluminium chloride are slowly introduced and the mixture is stirred at 80-83° C. until the evolution of HCl has ended (about 2 hours). The warm reaction solution is allowed to run into dil. hydrochloric acid with stirring, and the solid is filtered off with suction and washed with acetone/water until neutral. Drying is carried out at 100° C. in vacuo. 30.5 g (81.0% of theory) of 2,4-bis(2,4-dihydroxyphenyl)-6-(1-methylpyrrol-2-yl)-1,3,5-triazine are obtained as a yellow powder (m.p.>300° C.). The structure is in agreement with the 1H-NMR spectrum.

Workup

  1. customFriedel-Crafts acylation: In a 500 ml sulfonation flask having
  2. customa stirrer, dropping
  3. custom(about 2 hours)
  4. customThe warm reaction solution
  5. filtrationthe solid is filtered off with suction
  6. washwashed with acetone/water until neutral
  7. customDrying
  8. customis carried out at 100° C. in vacuo

Sources & evidence

ORD record
ord-e18a9a389b07414696b5846691098324
Source dataset
uspto-grants-1999_09
Patent number
US05955060

Reaction notes

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