1-Phenethylamine, (-)- → (S)-3-(4-methoxyphenyl)-[1,2,4]thiadiazole-5-carboxylic acid (1-phenylethyl)-amide

HRID 1080614Notes

Reaction equation

[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[N:13]=[C:12]([C:14]([O:16]CC)=O)[S:11][N:10]=2)=[CH:5][CH:4]=1.[C:19]1([C@@H:25]([NH2:27])[CH3:26])[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1>ClCCl>[C:19]1([C@@H:25]([NH:27][C:14]([C:12]2[S:11][N:10]=[C:9]([C:6]3[CH:5]=[CH:4][C:3]([O:2][CH3:1])=[CH:8][CH:7]=3)[N:13]=2)=[O:16])[CH3:26])[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1

Participants

Conditions

Temperature: 80 °C

Procedure

A mixture of (S)-1-phenylethyl)amine (1.21 g, 10 mmol) and ethyl 3-(4-methoxyphenyl)-[1,2,4]thiadiazole-5-carboxylate (1.32 g, 5 mmol) is stirred at 80° C. for 2 hours. A further portion of (S)-1-phenyl-ethylamine (0.5 g, 4 mmol) is added and the mixture is stirred for at 80° C. for a further 1.5 hours. The mixture is then cooled and dissolved in dichloromethane. The solution is washed with dilute sulphuric acid followed by water, and the organic phase is dried over magnesium sulphate. The solvent is evaporated in vacuo to give (S)-3-(4-methoxyphenyl)-[1,2,4]thiadiazole-5-carboxylic acid (1-phenylethyl)-amide (1.6 g, 94%) as colourless crystals, m.p. 143°-145° C.

Workup

stirringthe mixture is stirred for at 80° C. for a further 1.5 hours
temperatureThe mixture is then cooled
washThe solution is washed with dilute sulphuric acid
dry with materialthe organic phase is dried over magnesium sulphate
customThe solvent is evaporated in vacuo

Sources & evidence

ORD record: ord-1e502039d0384178aecbacf3d7666582
Source dataset: uspto-grants-1996_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05583092

Reaction notes

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