Phenethylamine → HCID 178429570, compound

HRID 1708881Notes

Reaction equation

C([N:3]([C:8]1[CH:13]=[CH:12][C:11]([C:14]2[CH:15]([CH3:21])[CH2:16][C:17](=[O:20])[NH:18][N:19]=2)=[CH:10][CH:9]=1)[C:4](=[NH:7])SC)#N.[CH2:22]([NH2:30])[CH2:23][C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1.[N:31]1C=CC=C[CH:32]=1>>[CH2:22]([NH:30][C:4](=[N:7][C:32]#[N:31])[NH:3][C:8]1[CH:9]=[CH:10][C:11]([C:14]2[CH:15]([CH3:21])[CH2:16][C:17](=[O:20])[NH:18][N:19]=2)=[CH:12][CH:13]=1)[CH2:23][C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1

Participants

Reactant 3

HCID 1001Phenethylamine

HCID 1049Pyridine

HCID 131715088HCID 131715088, compound

Product 1

HCID 178429570HCID 178429570, compound

Procedure

A stirred mixture of 6-(4-(N-cyano-S-methylisothioureido)phenyl)-5-methyl-4,5-dihydro-3(2H)-pyridazinone, (2 g), phenethylamine (8.4 ml) and pyridine (40 ml) was heated under reflux for 3 hours. The mixture was evaporated under reduced pressure to yield an oil, which on trituration with one normal acetic acid (17 ml) gave 1.1 g of a solid, m.p. 209°-210° C. Recrystallisation from ethanol gave the pure title compound, 0.64 g, m.p. 215°-217° C.

Workup

temperaturewas heated
temperatureunder reflux for 3 hours
customThe mixture was evaporated under reduced pressure
customto yield an oil, which on trituration with one normal acetic acid (17 ml)

Sources & evidence

ORD record: ord-d1a3d843fa194a14bd1a7b11a2e20718
Source dataset: uspto-grants-1990_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04946842

Reaction notes

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