Ethylenediamine → HCID 12049866, compound

HRID 1275675Notes

Reaction equation

HRID 1275675 reaction equation
[CH2:1]([NH2:4])[CH2:2][NH2:3].[Cl:5][C:6]1[C:14]2[C:9](=[CH:10][CH:11]=[CH:12][C:13]=2[N:15]=[C:16]=[S:17])[NH:8][CH:7]=1>C(Cl)Cl>[NH2:3][CH2:2][CH2:1][NH:4][C:16](=[S:17])[NH:15][C:13]1[CH:12]=[CH:11][CH:10]=[C:9]2[C:14]=1[C:6]([Cl:5])=[CH:7][NH:8]2

Participants

4

Reactant 2

HCID 3301EthylenediamineHCID 12049865HCID 12049865, compound

Product 1

HCID 12049866HCID 12049866, compoundYield 101.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Ethylenediamine (0.711 mL, 10.6 mmol) is added to a solution of 3-chloro-4-isothiocyanatoindole (0.370 g, 1.77 mmol) in methylene chloride (15 mL). The resulting solution is stirred at room temperature for 1 hour. The reaction mixture is concentrated by rotary evaporation and the crude material purified via silica gel column chromatography using 7% methanol (ammonium hydroxide treated)/methylene chloride as the eluent. The appropriate fractions are combined and the solvents removed by rotary evaporation to yield 0.484 g of 4-[N'-(2-aminoethyl)thioureido]-3-chloroindole as a white solid (90% yield).

Workup

  1. concentrationThe reaction mixture is concentrated by rotary evaporation
  2. customthe crude material purified via silica gel column chromatography
  3. customthe solvents removed by rotary evaporation

Sources & evidence

ORD record
ord-21255881065f4663b2292bb76375d7d5
Source dataset
uspto-grants-2000_12
Patent number
US06162818

Reaction notes

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