Ethylenediamine → 7-Methyl-6-(2-imidazolinylamino)indole

HRID 1937619Notes

Reaction equation

HRID 1937619 reaction equation
NCC[NH:4][C:5](=S)[NH:6][C:7]1[C:15](C)=C2C(C=CN2)=CC=1.[N:18]([C:21]1[C:29]([CH3:30])=[C:28]2[C:24]([CH:25]=[CH:26][NH:27]2)=[CH:23][CH:22]=1)=C=S.C(N)CN>C1(C)C=CC=CC=1>[CH3:30][C:29]1[C:21]([NH:18][N:6]2[CH2:7][CH2:15][N:4]=[CH:5]2)=[CH:22][CH:23]=[C:24]2[C:28]=1[NH:27][CH:26]=[CH:25]2

Participants

5

Reactant 3

HCID 3301EthylenediamineHCID 158963796-Isothiocyanato-7-methylindoleHCID 158963806-[-N'-(2-Aminoethyl)thioureido]-7-methylindole

Product 1

HCID 698310707-Methyl-6-(2-imidazolinylamino)indole

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Procedure

6-[-N′-(2-Aminoethyl)thioureido]-7-methylindole. A solution of 6-isothiocyanato-7-methylindole (0.85 g, 4.52 mmol) in 25 mL of toluene is added to a solution of ethylenediamine (1.06 mL, 15.8 mmol) in 50 mL of toluene. The milky white mixture is stirred for 30 minutes as the desired product precipitates. The reaction is filtered to yield 1.1 g of 6-[-N′-(2-aminoethyl)thioureido]-7-methylindole as a flaky white solid (99% yield).

Sources & evidence

ORD record
ord-c8a6f18e39e34dd280422a659211e549
Source dataset
uspto-grants-2002_05
Patent number
US06395764B1

Reaction notes

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