Acetic acid, 2-isothiocyanato-, ethyl ester → HCID 178516795, compound

HRID 446060

Reaction equation

HRID 446060 reaction equation
[NH2:1][CH2:2][CH2:3][C:4]1[N:8]=[CH:7][NH:6][CH:5]=1.[N:9]([CH2:12][C:13](OCC)=[O:14])=[C:10]=[S:11]>C(#N)C>[NH:6]1[CH:5]=[C:4]([CH2:3][CH2:2][N:1]2[C:13](=[O:14])[CH2:12][NH:9][C:10]2=[S:11])[N:8]=[CH:7]1

Participants

4

Reactant 2

HCID 32202Acetic acid, 2-isothiocyanato-, ethyl esterHCID 178419017HCID 178419017, compound

Product 1

HCID 178516795HCID 178516795, compoundYield 79.5%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
25 °C

Procedure

Histamine (111 mg, 1 mmol) and ethyl isothiocyanatoacetate (145 mg, 1 mmol) were dissolved in acetonitrile (6 mL), and the mixture was stirred at room temperature (25° C.) for 10 minutes. After the reaction was completed the solvent was removed by evaporation under reduced pressure, and the residue was subjected to silica gel column chromatography using chloroform/methanol (4/1 (volume ratio)) as an eluent, to give 3-(2-(1H-imidazol-4-yl)ethyl)-2-thioxoimidazolidin-4-one in a yield of 167 mg (yield 79.5%).

Workup

  1. customwas removed by evaporation under reduced pressure

Sources & evidence

ORD record
ord-71c6b9ea71f94b25a122e3db11fb8732
Source dataset
uspto-grants-2013_07
Patent number
US08476449B2

Linked notes

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