Acetone → 1-Methyl-N5-[3-[3-[(dimethylamino)methyl]phenoxy]propyl]-1H-1,2,4-triazole-3,5-diamine
Reaction equation
CS[C:3]([N:7]([CH3:16])[N:8]=CC1C=CC=CC=1)=[N:4][C:5]#[N:6].[NH2:17][CH2:18][CH2:19][CH2:20][O:21][C:22]1[CH:23]=[C:24]([CH2:28][N:29]([CH3:31])[CH3:30])[CH:25]=[CH:26][CH:27]=1.CC(C)=O.Cl>O>[CH3:16][N:7]1[C:3]([NH:17][CH2:18][CH2:19][CH2:20][O:21][C:22]2[CH:27]=[CH:26][CH:25]=[C:24]([CH2:28][N:29]([CH3:30])[CH3:31])[CH:23]=2)=[N:4][C:5]([NH2:6])=[N:8]1Participants
6
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Procedure
A mixture of N-cyano-1-methyl-2-(phenylmethylene)hydrazine-carboximidothioic acid methyl ester (166 mg) and 3-(3-aminopropoxy)-N,N-dimethylbenzenemethanamine (104 mg) was heated at 45° under a reduced pressure of 20 mm of mercury for 3 hr. Acetone was added, and the resulting solution treated with dilute hydrochloric acid for 1 hour at room temperature. The mixture was diluted with water, washed with ether, basified with excess sodium carbonate and extracted with ethyl acetate. Evaporation of the ethyl acetate extracts gave an oil which crystallised from ethyl acetate/light petroleum b.p. 60°-80° to give the title compound as colourless crystals m.p. 95°-96.5° (87 mg).
Workup
- temperaturewas heated at 45° under a reduced pressure of 20 mm of mercury for 3 hr
- washwashed with ether
- extractionextracted with ethyl acetate
- customEvaporation of the ethyl acetate extracts
- customgave an oil which
- customcrystallised from ethyl acetate/light petroleum b.p. 60°-80°
Sources & evidence
- ORD record
- ord-54787bbc82454d0294f90a9f07e5c2b2
- Source dataset
- uspto-grants-1988_08
- Patent number
- US04764612
Reaction notes
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