Toluene → (2-((Dimethylamino)methyl)thiazol-4-yl)methanol

HRID 2210237Notes

Reaction equation

HRID 2210237 reaction equation
O[C:2]1([CH2:11]Cl)[CH2:6][S:5][C:4]([CH2:7][N:8]([CH3:10])[CH3:9])=[N:3]1.C1(C)C=CC=CC=1.[OH-:20].[K+]>O>[CH3:9][N:8]([CH2:7][C:4]1[S:5][CH:6]=[C:2]([CH2:11][OH:20])[N:3]=1)[CH3:10]

Participants

5

Reactant 3

HCID 1140TolueneHCID 14797Potassium HydroxideHCID 103307024-Thiazolol, 4-(chloromethyl)-2-[(dimethylamino)methyl]-4,5-dihydro-

Product 1

HCID 1838020(2-((Dimethylamino)methyl)thiazol-4-yl)methanol

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a 100 ml, three-necked, flask equipped with an agitator and condensor were added 3.0 g (0.014 mol) of 4-hydroxy-4-chloromethyl-2-(dimethylaminomethyl) thiazoline (prepared as in Example 1), 47 ml of toluene, 1 ml of water and 0.79 g (0.014 mol) of solid potassium hydroxide. The resulting solution was stirred at room temperature for 45 minutes. A 1 μl sample of the reaction mixture was then removed from the flask and diluted according to the procedure described in Example 4. The HPLC assay set forth in Example 3 indicated that 72.6% of the thiazoline substrate had converted to the desired titled product.

Workup

  1. customTo a 100 ml, three-necked, flask equipped with an agitator and condensor
  2. customA 1 μl sample of the reaction mixture was then removed from the flask
  3. additiondiluted

Sources & evidence

ORD record
ord-25e532ff5698486f92475d287b8540ec
Source dataset
uspto-grants-1995_10
Patent number
US05457206

Reaction notes

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