Ethylenediamine → HCID 10931743, compound

HRID 1787548Notes

Reaction equation

HRID 1787548 reaction equation
[NH2:1][C:2]1[CH:9]=[CH:8][CH:7]=[CH:6][C:3]=1[C:4]#[N:5].[CH2:10](N)[CH2:11][NH2:12]>O.P12(SP3(SP(SP(S3)(S1)=S)(=S)S2)=S)=S>[NH:5]1[CH2:10][CH2:11][N:12]=[C:4]1[C:3]1[CH:6]=[CH:7][CH:8]=[CH:9][C:2]=1[NH2:1]

Participants

5

Reactant 2

HCID 3301EthylenediamineHCID 729132-Aminobenzonitrile

Product 1

HCID 10931743HCID 10931743, compoundYield 81.4%

Reagents, catalysts & solvents 2

HCID 14817Phosphorus sulfide (P2S5)CatalystHCID 962WaterSolvent

Conditions

Temperature
0 °C

Procedure

2-Aminobenzonitrile (9.00 g, 76.2 mmol) was added at 0° C. to ethylenediamine (25.5 ml, 381 mmol) in small portions with stirring. After phosphorus pentasulfide (200 mg, 0.900 mmol) was added, the mixture was stirred at 100° C. overnight. After cooling to 0° C., the reaction was diluted with water. The resulting white precipitate was collected by filtration, washed with water and diethyl ether, and dried under reduced pressure to give 2-(4,5-dihydro-1H-imidazol-2-yl)aniline (10.0 g, 81% yield).

Workup

  1. stirringthe mixture was stirred at 100° C. overnight
  2. filtrationThe resulting white precipitate was collected by filtration
  3. washwashed with water and diethyl ether
  4. customdried under reduced pressure

Sources & evidence

ORD record
ord-4bbac139a9334ce9bc2e18c324b691ec
Source dataset
uspto-grants-2009_03
Patent number
US07511041B2

Reaction notes

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