Ethylenediamine → HCID 15496493, compound

HRID 1755458Notes

Reaction equation

HRID 1755458 reaction equation
[CH2:1]([NH2:4])[CH2:2][NH2:3].[C:5]([N:13]=[C:14]=[S:15])(=[O:12])[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1>C(Cl)Cl>[CH2:1]([NH:4][C:14]([NH:13][C:5](=[O:12])[C:6]1[CH:7]=[CH:8][CH:9]=[CH:10][CH:11]=1)=[S:15])[CH2:2][NH:3][C:14]([NH:13][C:5](=[O:12])[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)=[S:15]

Participants

4

Reactant 2

HCID 3301EthylenediamineHCID 68284Benzoyl isothiocyanate

Product 1

HCID 15496493HCID 15496493, compoundYield 71.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To an ice cold solution of ethane-1,2-diamine (2.23 g, 37.1 mmol) in CH2Cl2 (100 mL) is added benzoyl isothiocyanate (12.41 g, 76 mmol) dropwise and the resulting suspension is stirred at room temp for 18 h. The reaction is filtered thru a ground glass frit and the resulting solid is washed with CH2Cl2 to give 10.2 g (71%) of the title compound as a white solid. LC/MS (Condition A): ret. T=3.67 min, (M+H)+ 387.13. 1H NMR (400 MHz, DMSO-d6) δ ppm 10.98 (2 H, br. s.), 7.86-8.01 (4 H, m), 7.60-7.72 (2 H, m), 7.47-7.58 (4 H, m), 3.88-4.09 (4 H, m).

Workup

  1. filtrationThe reaction is filtered thru a ground glass frit
  2. washthe resulting solid is washed with CH2Cl2

Sources & evidence

ORD record
ord-27011df39b6f4527b34891580bce217b
Source dataset
uspto-grants-2015_10
Patent number
US09169295B2

Reaction notes

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