Acetic acid 2-isothiocyanatoethylester → Acetic Acid 2-{3-[2-(3,5-dimethyl-phenyl)-1-thien-2-yl-ethyl]-thioureido}-ethyl Ester

HRID 1668280Notes

Reaction equation

HRID 1668280 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([CH2:9][CH:10]([NH2:16])[C:11]2[S:12][CH:13]=[CH:14][CH:15]=2)[CH:5]=[C:6]([CH3:8])[CH:7]=1.[N:17]([CH2:20][CH2:21][O:22][C:23](=[O:25])[CH3:24])=[C:18]=[S:19]>C1(C)C=CC=CC=1>[CH3:1][C:2]1[CH:3]=[C:4]([CH2:9][CH:10]([NH:16][C:18](=[S:19])[NH:17][CH2:20][CH2:21][O:22][C:23](=[O:25])[CH3:24])[C:11]2[S:12][CH:13]=[CH:14][CH:15]=2)[CH:5]=[C:6]([CH3:8])[CH:7]=1

Participants

4

Reactant 2

HCID 13552411Acetic acid 2-isothiocyanatoethylesterHCID 610284942-(3,5-Dimethyl-phenyl)-1-thien-2-yl-ethylamine

Product 1

HCID 24946566Acetic Acid 2-{3-[2-(3,5-dimethyl-phenyl)-1-thien-2-yl-ethyl]-thioureido}-ethyl EsterYield 25.7%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A solution of 2-(3,5-dimethyl-phenyl)-1-thiophen-2-yl-ethylamine (1.4 g, from example 1) and acetic acid 2-isothiocyanato-ethyl ester (0.75 g, prepared according to Collect. Czech. Chem. Commun. 1986, 51, 112-117) in toluene (15 ml) was stirred at room temperature for 12 h, evaporated and the residue purified by column chromatography to yield the product (0.5 g) as a yellowish oil.

Workup

  1. customevaporated
  2. customthe residue purified by column chromatography

Sources & evidence

ORD record
ord-4aaf099713a549dd9a1a6b9f871eaf25
Source dataset
uspto-grants-2011_08
Patent number
US07989394B2

Reaction notes

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