Triethylamine → N-[4-[3-(1-piperidinylmethyl)phenoxy]-2-butenyl]-1,3,4-thiadiazole-2,5-diamine

HRID 4636

Reaction equation

HRID 4636 reaction equation
[N:1]1([CH2:7][C:8]2[CH:9]=[C:10]([CH:17]=[CH:18][CH:19]=2)[O:11][CH2:12][CH:13]=[CH:14][CH2:15][NH2:16])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.C(N(CC)CC)C.Br[C:28]1[S:32][C:31]([NH2:33])=[N:30][N:29]=1>C1COCC1>[N:1]1([CH2:7][C:8]2[CH:9]=[C:10]([CH:17]=[CH:18][CH:19]=2)[O:11][CH2:12][CH:13]=[CH:14][CH2:15][NH:16][C:28]2[S:32][C:31]([NH2:33])=[N:30][N:29]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 36508832-Amino-5-bromo-1,3,4-thiadiazoleHCID 544322804-[3-(1-Piperidinylmethyl)phenoxy]2-butene-1-amine

Product 1

HCID 54123024N-[4-[3-(1-piperidinylmethyl)phenoxy]-2-butenyl]-1,3,4-thiadiazole-2,5-diamine

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

0.6 g (2.3 mmol) of 4-[3-(1-piperidinylmethyl)phenoxy]2-butene-1-amine, 0.35 ml of triethylamine and 0.42 g (2.3 mmol) of 5-bromo-1,3,4-thiadiazole-2-amin are heated under reflux in 20 ml of THF for 3 hours. Solid triethylammonium bromide is filtered off, the filtrate is concentrated by evaporation and the oily residue is purified by preparative layer chromatography.

Workup

  1. filtrationSolid triethylammonium bromide is filtered off
  2. concentrationthe filtrate is concentrated by evaporation
  3. customthe oily residue is purified by preparative layer chromatography

Sources & evidence

ORD record
ord-8eb4fc42e2804d748fd87ba8aac6a162
Source dataset
uspto-grants-1988_02
Patent number
US04727081

Linked notes

Loading…