Toluene → 7-Methyl-6-(2-imidazolinylamino)indole
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]2Participants
4
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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