Ethylenediamine → HCID 22461232, compound

HRID 1275668Notes

Reaction equation

HRID 1275668 reaction equation
[CH2:1]([NH2:4])[CH2:2][NH2:3].[N:5]([C:8]1[CH:16]=[CH:15][CH:14]=[C:13]2[C:9]=1[CH:10]=[CH:11][NH:12]2)=[C:6]=[S:7]>C(Cl)Cl>[NH2:3][CH2:2][CH2:1][NH:4][C:6](=[S:7])[NH:5][C:8]1[CH:16]=[CH:15][CH:14]=[C:13]2[C:9]=1[CH:10]=[CH:11][NH:12]2

Participants

4

Reactant 2

HCID 3301EthylenediamineHCID 22461249HCID 22461249, compound

Product 1

HCID 22461232HCID 22461232, compoundYield 91.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Ethylenediamine (0.289 mL, 4.33 mmol) is added to a solution of 4-isothiocyanatoindole (0.150 g, 0.866 mmol) in methylene chloride (10 mL). The clear solution becomes cloudy within a few seconds with the formation of a white precipitate. The reaction mixture is stirred for one hour followed by the removal of most of the methylene chloride by rotary evaporation. The mixture is filtered and the white precipitate is dried to afford 0.185 g of 4-[N'-(2-aminoethyl)thioureido]indole (91% yield).

Workup

  1. customwithin a few seconds
  2. customfollowed by the removal of most of the methylene chloride
  3. customby rotary evaporation
  4. filtrationThe mixture is filtered
  5. customthe white precipitate is dried

Sources & evidence

ORD record
ord-d32a954f05924c008d982c7b932a9fc4
Source dataset
uspto-grants-2000_12
Patent number
US06162818

Reaction notes

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