Reaction #46328

ord-3f76a09bbda543c59ed468a1f6be2b70

Reaction equation

CCCCCCNCCCCCC
Dihexylamine
CCOC1=NS(=O)(=O)N=C1OCC
3,4-diethyloxy-1,1-dioxo-1,2,5-thiadiazole
CCCCCCN(CCCCCC)C1=NS(=O)(=O)N=C1OCC
title intermediate
Yield 72.4%
CCCCCCN(CCCCCC)C1=NS(=O)(=O)N=C1OCC
4-(N,N-Di-n-hexylamino)-3-ethoxy-1,1-dioxo-1,2,5-thiadiazole
Yield 72.4%

Solvents

Conditions

Detailed conditions
See reaction.notes.procedure_details.

Workup

  1. 1
    OtherThe solvent was removed under reduced pressure
  2. 2
    Otherthe residue absorbed onto silica gel
  3. 3
    Otherand purified by flash column chromatography (silica, hexane:EtOAc 3:1)

Procedure

Dihexylamine (90 mg, 0.48 mmol) was added to a solution of 3,4-diethyloxy-1,1-dioxo-1,2,5-thiadiazole (100 mg, 0.48 mmol) in ethanol (5 mL) and the reaction stirred overnight at room temperature. The solvent was removed under reduced pressure and the residue absorbed onto silica gel; and purified by flash column chromatography (silica, hexane:EtOAc 3:1) to yield the title intermediate (120 mg, 72%).

Source

DOI: 10.6084/m9.figshare.5104873.v1Patent: US07741328B2uspto-grants-2010_06