Cyanuric chloride → HCID 21312532, compound

HRID 971911Notes

Reaction equation

HRID 971911 reaction equation
[N:1]1[C:8](Cl)=[N:7][C:5]([Cl:6])=[N:4][C:2]=1Cl.[NH2:10][C:11]1[CH:16]=[C:15]([CH3:17])[C:14]([OH:18])=[C:13]([C:19]([CH3:22])([CH3:21])[CH3:20])[CH:12]=1.[C:23](=[O:26])([O-])[O-].[Na+].[Na+]>CC(C)=O.O>[C:19]([C:13]1[CH:12]=[C:11]([CH:16]=[C:15]([CH3:17])[C:14]=1[OH:18])[NH:10][C:8]1[N:1]=[C:2]([NH:10][C:11]2[CH:16]=[C:15]([CH3:14])[C:23]([OH:26])=[C:13]([C:19]([CH3:22])([CH3:21])[CH3:20])[CH:12]=2)[N:4]=[C:5]([Cl:6])[N:7]=1)([CH3:22])([CH3:21])[CH3:20]

Participants

6

Reactant 3

HCID 7954Cyanuric chlorideHCID 10340Sodium CarbonateHCID 19609580HCID 19609580, compound

Product 1

HCID 21312532HCID 21312532, compoundYield 37.8%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolvent2×HCID 962WaterSolvent

Procedure

36.9 g of cyanuric chloride in 200 ml of boiling acetone were slowly poured into 400 ml of ice water, whilst stirring. The temperature was maintained between 0° and 5° C. by means of external cooling. 71.6 g of 4-amino-2-tert.-butyl-6-methylphenol in 100 ml of acetone and 42.4 g of sodium carbonate in 100 ml of water were simultaneously added at 10° C. The mixture was stirred at 10° C. for one hour and then at room temperature for 16 hours. The reaction mixture was then poured into ice water and the precipitate was filtered off and recrystallised from ethanol. In this way, it was possible to isolate 35.5 g of white 2,4-bis-(3-tert.-butyl-5-methyl-4-hydroxyanilino)-6-chloro-1,3,5-triazine which melts at 214° C.

Workup

  1. temperatureThe temperature was maintained between 0° and 5° C. by means of external cooling
  2. stirringThe mixture was stirred at 10° C. for one hour
  3. filtrationthe precipitate was filtered off
  4. customrecrystallised from ethanol

Sources & evidence

ORD record
ord-eb5fd1faeeff412cbba0c9bc4572c4ff
Source dataset
uspto-grants-1979_07
Patent number
US04161592

Reaction notes

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