N,N-Dimethylaniline → HCID 57357166, compound

HRID 1441910Notes

Reaction equation

HRID 1441910 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([CH3:8])=[CH:4][C:3]=1[N:9]1[N:13]=[C:12]2[CH:14]=[CH:15][CH:16]=[CH:17][C:11]2=[N:10]1.[CH2:18](N(CC)CC)C.CN(C)[C:27]1[CH:32]=[CH:31]C=CC=1>C(C(C)=O)C>[OH:1][C:2]1[CH:7]=[CH:6][C:5]([CH3:8])=[CH:4][C:3]=1[N:9]1[N:13]=[C:12]2[CH:14]=[CH:15][CH:16]=[CH:17][C:11]2=[N:10]1.[CH3:8][C:5]1[CH:6]=[CH:7][C:2]([O:1][CH:18]=[C:32]([CH3:31])[CH3:27])=[C:3]([N:9]2[N:13]=[C:12]3[CH:14]=[CH:15][CH:16]=[CH:17][C:11]3=[N:10]2)[CH:4]=1.[CH2:18]([N:10]1[C:11]2[CH:17]=[CH:16][CH:15]=[CH:14][C:12]=2[NH:13][N:9]1[C:3]1[CH:4]=[C:5]([CH3:8])[CH:6]=[CH:7][C:2]=1[OH:1])[C:32](=[CH2:31])[CH3:27]

Participants

7

Reactant 3

HCID 949N,N-DimethylanilineHCID 8471TriethylamineHCID 17113Drometrizole

Product 3

HCID 17113DrometrizoleHCID 20548403HCID 20548403, compoundHCID 57357166HCID 57357166, compoundYield 40%

Reagents, catalysts & solvents 1

HCID 6569Methyl Ethyl KetoneSolvent

Conditions

Temperature
80 °C

Procedure

10 g of 2-(2-hydroxy-5-methylphenyl) benzotriazole (0.044 moles), 4.5 g of the triethylamine (0.044 moles) and 16.1 g of N,N-dimethylaniline (0.13 moles) were introduced into a reacting chamber and stirred for 5 minutes to make a solution. 0.09 moles of 3-chloro-2-alkyl propylene were dissolved in the methyl ethyl ketone and then were added to the solution within 10 minutes into the reacting chamber where air inside the chamber was nitrogen gas. The solution was heated to 80° C. for 5 hours, further heated to 180° C. and held on for 3 hours to allow Claisen rearrangement before removing heat and allowing to cool to 80° C. Then, the solution was filtered using activated carbon A filtrate was recrystallized using 40 ml of isopropanol. Then, filter paper was used to filter a yellow recrystallized filtrate. The yellow recrystallized filtrate was isolated by column chromatography to obtain 3.1 g of 2-(2-hydroxyl-5-methylphenyl) benzotriazole, 0.2 g of 2-(5-methyl-2-(2-methyl-propenyloxy)-phenyl)-2H-benzotriazole, 4.9 g of 1-methallyl-2-(2′-hydroxyl-5′-methylphenyl) benzotriazole (yield: 40%) and 0.1 g of by-products including 2-benzotriazol-2-4 methyl-6-(2-methyl-propenyl)-phenol.

Workup

  1. additionwere added to the solution within 10 minutes into the reacting chamber where air inside the chamber
  2. temperaturefurther heated to 180° C.
  3. customheld on for 3 hours
  4. custombefore removing
  5. temperatureheat
  6. temperatureto cool to 80° C
  7. filtrationThen, the solution was filtered
  8. customwas recrystallized
  9. filtrationThen, filter paper
  10. filtrationto filter a yellow recrystallized filtrate
  11. customThe yellow recrystallized filtrate was isolated by column chromatography

Sources & evidence

ORD record
ord-76613adb6f40459fbf89f4371f767c65
Source dataset
uspto-grants-2010_02
Patent number
US07655805B2

Reaction notes

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