Reaction #302892

Reaction equation

2,3-dimethylbenzylamine

2-chloroethylisothiocyanate

→

title compound

Yield 76.0%

((2,3-dimethylphenyl)methyl)-1,3-thiazolin-2-ylamine hydrochloride

Yield 76.0%

Solvents

1,4-dioxane

Conditions

Workup

1. 1
   Temperatureto cool
2. 2
   Othera solid precipitate that had formed
3. 3
   Filtrationwas collected by filtration
4. 4
   WashThe solid was rinsed with diethyl ether
5. 5
   Otherwas dried under reduced pressure

Procedure

Under a dry nitrogen atmosphere, a stirred mixture of 5.56 grams (0.041 mole) of 2,3-dimethylbenzylamine and 5.0 grams (0.041 mole) of 2-chloroethylisothiocyanate in 100 mL of 1,4-dioxane was heated to 80° C. where it stirred for about 18 hours. The reaction mixture was allowed to cool and a solid precipitate that had formed was collected by filtration. The solid was rinsed with diethyl ether and was dried under reduced pressure to yield 8.0 grams of the title compound. The NMR spectrum was consistent with the proposed structure.

Source