Reaktion #363791

Reaktionsgleichung

2,3-dimethyl-6-nitroaniline

2,3-dimethylacetanilide

acetamide

aniline

1-chloromethylcyclopentanamine HCl salt

2,3-Dimethylaniline

2-hydroxyethylamine

1-Chloromethylcyclopentanamine HCl salt

2,3-dimethyl-6-nitrophenyl isothiocyanate

→

1-Hydroxymethylcyclopentanamine

2-(2,3-dimethyl-6-nitrophenylimino)-3-thia-1-azaspiro[4.4]nonane

Reaktionsbedingungen

Vorschrift

2,3-Dimethylaniline was protected as 2,3-dimethylacetanilide according to Method A2a, step 1. The acetamide was converted to 2,3-dimethyl-6-nitroaniline, then deprotected according to Method A2a, step 2. The aniline was converted to 2,-dimethyl-6-nitrophenyl isothiocyanate according to Method A2a, step 3. 1-Hydroxymethylcyclopentanamine was prepared according to Method B1c. The 2-hydroxyethylamine was converted to 1-chloromethylcyclopentanamine HCl salt according to Method B7e. 1-Chloromethylcyclopentanamine HCl salt was reacted with 2,3-dimethyl-6-nitrophenyl isothiocyanate according to Method C1e to give 2-(2,3-dimethyl-6-nitrophenylimino)-3-thia-1-azaspiro[4.4]nonane. The thiazolidine was reacted with cyclopentyl bromide according to Method D2b to give 2-(2,3-dimethyl-6-nitrophenylimino)-1-cyclopentyl-3-thia-1-azaspiro[4.4]nonane.

Quelle