Nitrogen → 1-(3-Cyano-4-methoxyphenyl)-5-[4-(methylthio)phenyl]-2-pyrazoline-3-amine

HRID 429323Notes

Reaction equation

Cl.[C:2]([C:4]1[CH:5]=[C:6]([NH:12][NH2:13])[CH:7]=[CH:8][C:9]=1[O:10][CH3:11])#[N:3].[CH3:14][S:15][C:16]1[CH:21]=[CH:20][C:19]([CH:22]=[CH:23][C:24]#[N:25])=[CH:18][CH:17]=1.C[O-].[Na+].N#N>CO.O.C(OCC)(=O)C>[C:2]([C:4]1[CH:5]=[C:6]([N:12]2[CH:22]([C:19]3[CH:20]=[CH:21][C:16]([S:15][CH3:14])=[CH:17][CH:18]=3)[CH2:23][C:24]([NH2:25])=[N:13]2)[CH:7]=[CH:8][C:9]=1[O:10][CH3:11])#[N:3]

Participants

Conditions

Temperature: 140 °C

Procedure

A stirred mixture of (3-cyano-4-methoxyphenyl)hydrazine hydrochloride (3.7 g), 3-[4-(methylthio)phenyl]acrylonitrile (2.3 g) and sodium methoxide (0.9 g) in methanol 13 ml was gradually heated to 140° C. under atmospheric pressure and N2 atmosphere, and continued to heat for 8 hours at 140° C. Ethyl acetate and water were added to the reaction mixture. The organic layer was separated, washed with brine, dried over magnesium sulfate, and concentrated under reduced pressure to give crude 1-(3-cyano-4-methoxyphenyl)-5-[4-(methylthio)-phenyl]-2-pyrazoline-3-amine (4.0 g).

Workup

customThe organic layer was separated
washwashed with brine
dry with materialdried over magnesium sulfate
concentrationconcentrated under reduced pressure

Sources & evidence

ORD record: ord-7b4b74057c9f41a9ae4432725fa8f793
Source dataset: uspto-grants-2001_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06316485B1

Reaction notes

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