Sodium Hydroxide → HCID 22159365, compound

HRID 1089441Notes

Reaction equation

HRID 1089441 reaction equation
[Cl:1][C:2]1[N:7]=[CH:6][C:5]([C:8]([CH3:12])([CH3:11])[CH2:9][OH:10])=[CH:4][CH:3]=1.[O:13]([C:20]1[CH:21]=[C:22]([CH:25]=[CH:26][CH:27]=1)[CH2:23]Br)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.[OH-].[Na+].O.N>C1(C)C=CC=CC=1.S([O-])(O)(=O)=O.C([N+](CCCC)(CCCC)CCCC)CCC.O.CO>[O:13]([C:20]1[CH:21]=[C:22]([CH:25]=[CH:26][CH:27]=1)[CH2:23][O:10][CH2:9][C:8]([C:5]1[CH:6]=[N:7][C:2]([Cl:1])=[CH:3][CH:4]=1)([CH3:12])[CH3:11])[C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=1

Participants

9

Reactant 4

HCID 14798Sodium HydroxideHCID 945441-(Bromomethyl)-3-phenoxybenzeneHCID 12896473Azane;hydrateHCID 221593551649468-09-6

Product 1

HCID 22159365HCID 22159365, compound

Reagents, catalysts & solvents 4

HCID 94433Tetrabutylammonium hydrogen sulfateCatalystHCID 887MethanolSolventHCID 962WaterSolventHCID 1140TolueneSolvent2×

Procedure

1.9 g (10.2 mmol) of 2-(6-chloro-pyrid-3-yl)-2-methylpropanol are dissolved in 15 ml of toluene, 2.7 g (10.3 mmol) of 3-phenoxy-benzyl bromide are added and a solution of 0.6 g (1.8 mmol) of tetra-n-butylammonium hydrogen sulfate in 5 g of 50% strength sodium hydroxide solution is added. The mixture is stirred at 70°-80° C. for 2 hours, mixed with a mixture of 2 ml of methanol and 2 ml of concentrated ammonia water and finally all distributed between water and toluene. The organic phase is washed with ammonium chloride solution, the solvent is removed and the crude product is purified through a silica gel column. 2.4 g (62.9% of theory) of a weakly yellowish oil are thus obtained. The oil is distilled in the bulb tube at 0.03 mbar and 230°-240° C. apparatus temperature.

Workup

  1. washThe organic phase is washed with ammonium chloride solution
  2. customthe solvent is removed
  3. customthe crude product is purified through a silica gel column
  4. custom2.4 g (62.9% of theory) of a weakly yellowish oil are thus obtained
  5. distillationThe oil is distilled in the bulb tube at 0.03 mbar and 230°-240° C. apparatus temperature

Sources & evidence

ORD record
ord-249405c6a89148e2807de39e8cc55f78
Source dataset
uspto-grants-1990_10
Patent number
US04966902

Reaction notes

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