Phenol → HCID 90449221, compound

HRID 2274164Notes

Reaction equation

HRID 2274164 reaction equation
[CH2:1]([O:8][C:9]1[N:14]=[C:13](Cl)[N:12]=[C:11]([Cl:16])[N:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:17]1([OH:23])[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.C(N(CC)C(C)C)(C)C>ClCCl>[CH2:1]([O:8][C:9]1[N:10]=[C:11]([Cl:16])[N:12]=[C:13]([O:23][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[N:14]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 996PhenolHCID 356262-benzyloxy-4,6-dichloro-[1,3,5]triazineHCID 81531Diisopropylethylamine

Product 1

HCID 90449221HCID 90449221, compoundYield 94.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Procedure

Next, 5.70 mL of dichloromethane solution containing 896.2 mg (3.50 m mol) of 6-benzyloxy-2,4-dichloro-1,3,5-triazine, 2.00 mL of dichloromethane, 365.0 mg (3.88 m mol) of phenol and 0.738 mL (4.23 m mol) of N,N-diisopropylethylamine was added to a 30 mL eggplant flask, and reacted at 0 degree under a nitrogen atmosphere for 6 hours. After the reaction, 20 mL of dichloromethane was added, which was washed with 20 mL of 1 N hydrochloric acid, 20 mL of 1 N hydrochloric acid, 20 mL of water and 20 mL of saturated salt water. A resulting organic phase was dried by magnesium sulfate, from which dichloromethane was distilled away, and the residue was recrystallized to obtain 1033.2 mg of 6-benzyloxy-2-chloro-4-phenoxy-1,3,5-triazine (yield: 94%).

Workup

  1. additionwas added to a 30 mL eggplant flask
  2. customreacted at 0 degree under a nitrogen atmosphere for 6 hours
  3. additionwas added
  4. washwhich was washed with 20 mL of 1 N hydrochloric acid, 20 mL of 1 N hydrochloric acid, 20 mL of water and 20 mL of saturated salt water
  5. dry with materialA resulting organic phase was dried by magnesium sulfate, from which dichloromethane
  6. distillationwas distilled away
  7. customthe residue was recrystallized

Sources & evidence

ORD record
ord-899d01437bb84b039b7dc33f361d3b16
Source dataset
uspto-grants-2015_09
Patent number
US09126954B2

Reaction notes

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