Dimethyl N-cyanodithioiminocarbonate → N-cyano-N'-[2-((3-bromo-2-pyridyl)methylthio)ethyl]-S-methylisothiourea
Reaction equation
CS[C:3](=[N:6][C:7]#[N:8])[S:4][CH3:5].[NH2:9][CH2:10][CH2:11][S:12][CH2:13][C:14]1[C:19]([Br:20])=[CH:18][CH:17]=[CH:16][N:15]=1>>[C:7]([NH:6][C:3](=[N:9][CH2:10][CH2:11][S:12][CH2:13][C:14]1[C:19]([Br:20])=[CH:18][CH:17]=[CH:16][N:15]=1)[S:4][CH3:5])#[N:8]Participants
3
Procedure
Reaction of dimethylcyanodithioimidocarbonate with 2-((2-aminoethyl)thiomethyl)-3-bromopyridine by the procedure described in Example 3 (d) gave N-cyano-N'-[2-((3-bromo-2-pyridyl)methylthio)ethyl]-S-methylisothiourea and a mixture of this compound (1.4 g.) and 3-bromo-2-((2-aminoethyl)thiomethyl)pyridine (2.0 g.) was heated at 140° for 6 hours. The product crystallised upon treatment with isopropyl acetate and was recrystallised from aqueous isopropanol to give the title compound (1.1 g.), m.p. 118°-119°. (Found: C, 40.0; H, 3.8; N, 15.9; Br, 29.5; S, 11.9% C18H20N6Br2S2 requires: C, 39.7; H, 3.7; N, 15; Br, 29.4; S, 11.8%)
Sources & evidence
- ORD record
- ord-30d6d151de3b4d699fe049be28d6ca09
- Source dataset
- uspto-grants-1980_07
- Patent number
- US04215125
Reaction notes
Loading…