Hydrochloric Acid → 1-(2-Aminoethyl)-3-(2,6-dichlorophenyl)thiourea

HRID 243522

Reaction equation

HRID 243522 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([Cl:8])[C:3]=1[N:9]=[C:10]=[S:11].C1COCC1.[CH2:17]([NH2:20])[CH2:18][NH2:19].Cl>O>[NH2:19][CH2:18][CH2:17][NH:20][C:10]([NH:9][C:3]1[C:2]([Cl:1])=[CH:7][CH:6]=[CH:5][C:4]=1[Cl:8])=[S:11]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 3301EthylenediamineHCID 8028Tetrahydrofuran2×HCID 1232391,3-Dichloro-2-isothiocyanatobenzene

Product 1

HCID 30367871-(2-Aminoethyl)-3-(2,6-dichlorophenyl)thiourea

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A solution of 2,6-dichlorophenyl isothiocyanate (500 mg) and THF (5 ml) was added dropwise under argon within 20 minutes to a solution of ethylenediamine (3.68 g) and abs. THF (4 ml). After stirring for a further 30 min, the mixture was added to water, acidified with 10% HCl and extracted three times with ethyl acetate. The aqueous phase was made basic using saturated potassium carbonate solution, and extracted three times with ethyl acetate. The combined organic phases were dried over magnesium sulfate, the solvent was removed under reduced pressure and the residue was co-evaporated twice with toluene. After drying in high vacuum, the desired product was obtained as a white solid (532 mg).

Workup

  1. extractionextracted three times with ethyl acetate
  2. extractionextracted three times with ethyl acetate
  3. dry with materialThe combined organic phases were dried over magnesium sulfate
  4. customthe solvent was removed under reduced pressure
  5. customAfter drying in high vacuum

Sources & evidence

ORD record
ord-0c9352ce51844b3ab9f9a5a1d8a82163
Source dataset
uspto-grants-2014_02
Patent number
US08653259B2

Linked notes

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