Hydrochloric Acid → 1-(2-Aminoethyl)-3-phenylthiourea

HRID 243516Notes

Reaction equation

HRID 243516 reaction equation
[C:1]1([N:7]=[C:8]=[S:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C1COCC1.[CH2:15]([NH2:18])[CH2:16][NH2:17].Cl>O>[NH2:17][CH2:16][CH2:15][NH:18][C:8]([NH:7][C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1)=[S:9]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 3301EthylenediamineHCID 7673Phenyl IsothiocyanateHCID 8028Tetrahydrofuran2×

Product 1

HCID 21434541-(2-Aminoethyl)-3-phenylthiourea

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A solution of phenyl isothiocyanate (500 mg) in abs. THF (6 ml) was added dropwise over 20 minutes under argon to a solution of ethylenediamine (5.56 g) in abs. THF (6 ml). Afterwards, the reaction mixture was added to water, acidified with 10% HCl and extracted with ethyl acetate. The aqueous phase was then basified with potassium carbonate and extracted three times with ethyl acetate. The combined organic phases were dried over magnesium sulfate, filtered and concentrated. Subsequently, co-evaporation with toluene was effected twice. 650 mg of the desired product remained.

Workup

  1. extractionextracted with ethyl acetate
  2. extractionextracted three times with ethyl acetate
  3. dry with materialThe combined organic phases were dried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-41d5c877d2284ab7ae670d653f6e9554
Source dataset
uspto-grants-2014_02
Patent number
US08653259B2

Reaction notes

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