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

HRID 1275658Notes

Reaction equation

HRID 1275658 reaction equation
[N:1]([C:4]1[C:12]([CH3:13])=[C:11]2[C:7]([CH:8]=[CH:9][NH:10]2)=[CH:6][CH:5]=1)=C=S.[CH2:14]([NH2:17])[CH2:15][NH2:16].[C:18]1(C)C=CC=CC=1>>[CH3:13][C:12]1[C:4]([NH:1][N:16]2[CH2:15][CH2:14][N:17]=[CH:18]2)=[CH:5][CH:6]=[C:7]2[C:11]=1[NH:10][CH:9]=[CH:8]2

Participants

4

Reactant 3

HCID 1140Toluene2×HCID 3301EthylenediamineHCID 158963796-Isothiocyanato-7-methylindole

Product 1

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

Procedure

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-3a97ea4877b54c01b86c028b4180851e
Source dataset
uspto-grants-2000_12
Patent number
US06162818

Reaction notes

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