Isopropanol → HCID 19991773, compound

HRID 346004Notes

Reaction equation

HRID 346004 reaction equation
Cl[C:2]1[N:7]=[C:6]([O:8][CH:9]([CH3:11])[CH3:10])[N:5]=[C:4]([N:12]2[C:17]([CH3:19])([CH3:18])[CH2:16][CH2:15][CH2:14][C:13]2([CH3:21])[CH3:20])[N:3]=1.[OH-].[K+].[CH:24]([OH:27])([CH3:26])[CH3:25]>S([O-])(O)(=O)=O.C([N+](CCCC)(CCCC)CCCC)CCC.C1(C)C=CC=CC=1.O>[CH:24]([O:27][C:2]1[N:7]=[C:6]([O:8][CH:9]([CH3:11])[CH3:10])[N:5]=[C:4]([N:12]2[C:17]([CH3:19])([CH3:18])[CH2:16][CH2:15][CH2:14][C:13]2([CH3:21])[CH3:20])[N:3]=1)([CH3:26])[CH3:25]

Participants

7

Reactant 3

HCID 3776IsopropanolHCID 14797Potassium HydroxideHCID 19991784HCID 19991784, compound2×

Product 1

HCID 19991773HCID 19991773, compound

Reagents, catalysts & solvents 3

HCID 94433Tetrabutylammonium hydrogen sulfateCatalystHCID 962WaterSolventHCID 1140TolueneSolvent2×

Procedure

12.5 g of 2-chloro-4-isopropyloxy-6-(2,2,6,6-tetramethylpiperidin-1-yl)- 1,3,5-triazine (product from Example 55), 11.2 g of finely pulverized potassium hydroxide and 0.7 g of tetrabutylammonium hydrogen sulfate are initially introduced in 60 ml of toluene. 2.6 g of isopropanol are added dropwise during the course of 15 minutes to this orange-colored suspension: weakly exothermic reaction to about 30+. The pale brown contents of the flask are stirred at 60° for 8 hours, cooled to 0°-5°, and diluted with 80 ml of water and then with 40 ml of toluene. The brown, aqueous phase is separated off from the colorless, organic phase and the latter is washed four times, each with 80 ml of water, dried over sodium sulfate and completely evaporated in vacuo. A weakly yellowish oil is obtained which solidifies after a short time to give 2,4-bis-isopropyloxy-6-(2,2,6,6-tetramethylpiperidin-1-yl)-1,3,5-triazine with a melting range of 70°-98°.

Workup

  1. customweakly exothermic reaction to about 30+
  2. temperaturecooled to 0°-5°
  3. customThe brown, aqueous phase is separated off from the colorless, organic phase
  4. washthe latter is washed four times
  5. dry with materialeach with 80 ml of water, dried over sodium sulfate
  6. customcompletely evaporated in vacuo
  7. customA weakly yellowish oil is obtained which

Sources & evidence

ORD record
ord-56d40c0552ae4799b48bd82a9143eeb9
Source dataset
uspto-grants-1991_10
Patent number
US05059689

Reaction notes

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