Triethylamine → N-(tert-butyl)-N'-[(1RS)-1-hydroxymethyl-2-(2-pyrazinyl)ethyl]thiourea

HRID 47762Notes

Reaction equation

C(N(CC)CC)C.Cl.Cl.[NH2:10][CH:11]([CH2:14][C:15]1[CH:20]=[N:19][CH:18]=[CH:17][N:16]=1)[CH2:12][OH:13].[C:21]([N:25]=[C:26]=[S:27])([CH3:24])([CH3:23])[CH3:22]>C(O)C>[C:21]([NH:25][C:26]([NH:10][CH:11]([CH2:12][OH:13])[CH2:14][C:15]1[CH:20]=[N:19][CH:18]=[CH:17][N:16]=1)=[S:27])([CH3:24])([CH3:23])[CH3:22]

Participants

Conditions

Temperature: 50 °C

Procedure

11.2 cm3 of triethylamine are added with stirring to a solution of 7.91 g of (2RS)-2-amino-3-(2-pyrazinyl)-1-propanol dihydrochloride in 80 cm3 of ethanol, followed by addition of 7.2 cm3 of tert-butyl isothiocyanate. The mixture is heated at a temperature in the region of 50° C. for 18 hours. After cooling, the reaction medium is concentrated under reduced pressure (1 kPa) at a temperature in the region of 40° C., taken up in 100 cm3 of water and extracted with dichloromethane. The organic phases are combined, washed with 50 cm3 of water, dried over magnesium sulfate, filtered and then concentrated under reduced pressure (1 kPa) at a temperature in the region of 40° C. 7.2 g of N-(tert-butyl)-N′-[(1RS)-1-hydroxymethyl-2-(2-pyrazinyl)-ethyl]thiourea are obtained in the form of a colorless paste [mass spectrum: DCI m/z=269 MH+].

Workup

temperatureAfter cooling
concentrationthe reaction medium is concentrated under reduced pressure (1 kPa) at a temperature in the region of 40° C.
extractionextracted with dichloromethane
washwashed with 50 cm3 of water
dry with materialdried over magnesium sulfate
filtrationfiltered
concentrationconcentrated under reduced pressure (1 kPa) at a temperature in the region of 40° C

Sources & evidence

ORD record: ord-fe016cb775cb4418a92582a3bd84981b
Source dataset: uspto-grants-2004_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06699895B2

Reaction notes

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