Sodium hydride → 2-Bromomethyl-2-(4-chlorophenyl)-4-[2-chloro-4-(N,N-dimethylaminomethyl)-6-methylphenoxymethyl]-1,3-dioxolane

HRID 1074427Notes

Reaction equation

HRID 1074427 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([CH2:8][N:9]([CH3:11])[CH3:10])[CH:5]=[C:4]([CH3:12])[C:3]=1[OH:13].[H-].[Na+].[H][H].CS(O[CH2:23][CH:24]1[CH2:28][O:27][C:26]([CH2:36][Br:37])([C:29]2[CH:34]=[CH:33][C:32]([Cl:35])=[CH:31][CH:30]=2)[O:25]1)(=O)=O>CN(C)C=O>[Br:37][CH2:36][C:26]1([C:29]2[CH:34]=[CH:33][C:32]([Cl:35])=[CH:31][CH:30]=2)[O:25][CH:24]([CH2:23][O:13][C:3]2[C:4]([CH3:12])=[CH:5][C:6]([CH2:8][N:9]([CH3:10])[CH3:11])=[CH:7][C:2]=2[Cl:1])[CH2:28][O:27]1

Participants

6

Reactant 4

HCID 24758Sodium hydrideHCID 30681252,4-Xylenol, 6-chloro-alpha(sup 4)-(dimethylamino)-HCID 155764512-Bromomethyl-2-(4-chlorophenyl)-1,3-dioxolan-4-ylmethyl methanesulfonateHCID 178418361HCID 178418361, compound

Product 1

HCID 542494812-Bromomethyl-2-(4-chlorophenyl)-4-[2-chloro-4-(N,N-dimethylaminomethyl)-6-methylphenoxymethyl]-1,3-dioxolane

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

4 g=20 mmoles of 2-chloro-4-(N,N-dimethylaminomethyl)-6-methylphenol are added in portions, while cooling with an ice bath and stirring, to a suspension of 0.6 g=20 mmoles of sodium hydride (an 80% strength dispersion in oil) in 30 ml of absolute dimethylformamide at such a rate that the temperature does not exceed 20° C. Stirring is continued at 20° C. until the evolution of hydrogen is complete, 8.26 g=20 mmoles of 2-bromomethyl-2-(4-chlorophenyl)-1,3-dioxolan-4-ylmethyl methanesulfonate (compound of the formula (IV)) are then introduced in portions, stirring is continued for 7 hours at 60° C. and the mixture is worked up as described in Example 1a. This gives 7 g (71% of theory) of a highly viscous, noncrystalline oil.

Workup

  1. temperaturewhile cooling with an ice bath
  2. customdoes not exceed 20° C
  3. stirringstirring

Sources & evidence

ORD record
ord-c6d9e0f758734ffeb89fd3933bcb167c
Source dataset
uspto-grants-1983_07
Patent number
US04391805

Reaction notes

Loading…