Acetone → HCID 178478359, compound

HRID 1066442Notes

Reaction equation

HRID 1066442 reaction equation
[N:1]1[C:8](Cl)=[N:7][C:5]([Cl:6])=[N:4][C:2]=1[Cl:3].CC(C)=O.[OH-].[Na+].[C:16]1([CH:23]=[CH:22][CH:21]=[C:19]([OH:20])[CH:18]=1)[OH:17]>O>[Cl:6][C:5]1([O:17][C:16]2[CH:23]=[CH:22][CH:21]=[C:19]([O:20][C:5]3([Cl:6])[N:4]=[C:2]([Cl:3])[N:1]=[CH:8][NH:7]3)[CH:18]=2)[N:4]=[C:2]([Cl:3])[N:1]=[CH:8][NH:7]1

Participants

6

Reactant 4

HCID 180AcetoneHCID 5054Resorcinol2×HCID 7954Cyanuric chlorideHCID 14798Sodium Hydroxide3×

Product 1

HCID 178478359HCID 178478359, compoundYield 890.2%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

A 1 L jacketed reaction flask equipped with a gas inlet, a mechanical stirrer, two liquid inlets and a condenser is purged with argon and charged with 37.3 g (0.0200 mol) of cyanuric chloride and 300 mL of acetone. The stirred mixture is cooled below −15° C. and 30 mL of deionized water are added. A 10% aqueous sodium hydroxide solution (88 g) are added over a 66-minute period via a peristaltic pump. Six minutes after the sodium hydroxide addition is started, a resorcinol solution (11.0 g, 0.100 mol in 50 mL of water) addition is begun also via a peristaltic pump. The resorcinol solution is then added over a 60-minute period concurrent with the sodium hydroxide solution. A slight exotherm occurs causing the temperature to rise to −12° C. The mixture is then stirred for an additional four hours at between −15° C. and −20° C. A 200 mL poriton of water is added and the white solids formed are collected by vacuum filtration followed by washing with three 50 mL portions of water. The solids are dried at 60° C. under reduced pressure to afford 36.5 g of the title compound as a white solid.

Workup

  1. customreaction flask
  2. customequipped with a gas inlet, a mechanical stirrer
  3. customtwo liquid inlets and a condenser is purged with argon
  4. temperatureThe stirred mixture is cooled below −15° C.
  5. customto rise to −12° C
  6. customthe white solids formed
  7. filtrationare collected by vacuum filtration
  8. washby washing with three 50 mL portions of water
  9. customThe solids are dried at 60° C. under reduced pressure

Sources & evidence

ORD record
ord-8c9eb74c86cf450fb4dcc90c560d2ed6
Source dataset
uspto-grants-2001_06
Patent number
US06242598B1

Reaction notes

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