2,4-Dichloro-6-methyl-1,3,5-triazine → HCID 15547795, compound

HRID 2268010Notes

Reaction equation

HRID 2268010 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([C:11]([CH3:14])([CH3:13])[OH:12])[CH:5]=[C:6]([O:9][CH3:10])[C:7]=1[OH:8].[Cl:15][C:16]1[N:21]=[C:20](Cl)[N:19]=[C:18]([CH3:23])[N:17]=1>[OH-].[Na+].O.C(#N)C>[Br:1][C:2]1[CH:3]=[C:4]([C:11]([CH3:14])([CH3:13])[OH:12])[CH:5]=[C:6]([O:9][CH3:10])[C:7]=1[O:8][C:20]1[N:21]=[C:16]([Cl:15])[N:17]=[C:18]([CH3:23])[N:19]=1

Participants

6

Reactant 2

HCID 160832,4-Dichloro-6-methyl-1,3,5-triazineHCID 15547804HCID 15547804, compound

Product 1

HCID 15547795HCID 15547795, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6342AcetonitrileSolventHCID 14798Sodium HydroxideSolvent

Procedure

3-bromo-4-hydroxy-5-methoxy-a,a-dimethylbenzenemethanol (1.16 g) was dissolved in 10% NaOH (1.78 g) and 5 mL of water. The solvent was stripped under reduced pressure. The salt was taken up in 50 mL acetonitrile and cooled to 0°-5° C. 2,4-dichloro-6-methyl-1,3,5-triazine (0.61g) was added and the mixture was stirred at 0°-5° C. for 1 hour. The solvent was removed under reduced pressure and the residue was extracted with methylene chloride. The extracts were combined and stripped under reduced pressure to yield 3-bromo-4-[[4-chloro-6-methyl-1,3,5-triazin-2-yl]oxy]-5-methoxy-a,a-dimethylbenzenemethanol.

Workup

  1. temperaturecooled to 0°-5° C
  2. customThe solvent was removed under reduced pressure
  3. extractionthe residue was extracted with methylene chloride

Sources & evidence

ORD record
ord-811a2cb468ff45b3a315ed66ee900124
Source dataset
uspto-grants-2001_12
Patent number
US06326368B1

Reaction notes

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