4-Aminobenzoic Acid → 4,4'-[(6-Chloro-1,3,5-triazine-2,4-diyl)diazanediyl]dibenzoic acid

HRID 1066697Notes

Reaction equation

HRID 1066697 reaction equation
[NH2:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[CH:4][CH:3]=1.[N:11]1[C:18](Cl)=[N:17][C:15](Cl)=[N:14][C:12]=1[Cl:13].[C:20](=[O:23])([O-])[O-:21].[Na+].[Na+]>CC(C)=O.O>[Cl:13][C:12]1[N:11]=[C:18]([NH:1][C:2]2[CH:10]=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[CH:4][CH:3]=2)[N:17]=[C:15]([NH:1][C:2]2[CH:10]=[CH:9][C:5]([C:20]([OH:21])=[O:23])=[CH:4][CH:3]=2)[N:14]=1

Participants

6

Reactant 3

HCID 9784-Aminobenzoic AcidHCID 7954Cyanuric chlorideHCID 10340Sodium Carbonate

Product 1

HCID 123796414,4'-[(6-Chloro-1,3,5-triazine-2,4-diyl)diazanediyl]dibenzoic acidYield 101.9%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 962WaterSolvent2×

Procedure

To 350 grams of 4-aminobenzoic acid and 7437.5 grams of water at 11° C. was added a solution of 157.1 grams of cyanuric chloride in 739.93 grams of acetone and a solution of 135.2 grams of sodium carbonate in 993.5 grams of water simultaneously dropwise at a rate such that the temperature was maintained below 15° C. Following the addition the batch was allowed to mix for one hour at 15° C. and then warmed to room temperature. The solid was collected, washed with water and acetone and dried to give 335 grams of 4,4′-[(6-chloro-1,3,5-triazine-2,4-diyl)diimino]bis-benzoic acid (1) as a white/tan solid.

Workup

  1. additionthe addition the batch
  2. additionto mix for one hour at 15° C.
  3. customThe solid was collected
  4. washwashed with water and acetone
  5. customdried

Sources & evidence

ORD record
ord-eee7aa57a695453b97aab41868f8f911
Source dataset
uspto-grants-2001_06
Patent number
US06245399B1

Reaction notes

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