Triethylamine → N-(tert-butyl)-N'-[(1S)-2-hydroxy-1-(3-nitrobenzyl)ethyl]thiourea
Reaction equation
Cl.[NH2:2][C@@H:3]([CH2:6][C:7]1[CH:12]=[CH:11][CH:10]=[C:9]([N+:13]([O-:15])=[O:14])[CH:8]=1)[CH2:4][OH:5].[C:16]([N:20]=[C:21]=[S:22])([CH3:19])([CH3:18])[CH3:17].C(N(CC)CC)C>C(O)C>[C:16]([NH:20][C:21]([NH:2][C@@H:3]([CH2:6][C:7]1[CH:12]=[CH:11][CH:10]=[C:9]([N+:13]([O-:15])=[O:14])[CH:8]=1)[CH2:4][OH:5])=[S:22])([CH3:19])([CH3:18])[CH3:17]Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 20 °C
Procedure
The process is performed as in Example 2, starting with 5.65 g of (2S)-2-amino-3-(3-nitrophenyl)-1-propanol hydrochloride, 3.7 cm3 of tert-butyl isothiocyanate and 3.41 cm3 of triethylamine in 60 cm3 of ethanol. After stirring for 3 days at a temperature in the region of 20° C. and then heating for 30 minutes at a temperature in the region of 60° C., 3.7 cm3 of tert-butyl isothiocyanate are added to the reaction medium and heating is then continued for a further 3 hours at the same temperature. After an identical work-up, 6.45 g of N-(tert-butyl)-N′-[(1S)-2-hydroxy-1-(3-nitrobenzyl)ethyl]thiourea are obtained in the form of a yellow foam. (Rf=0.61 in a 40/5/0.5 by volume mixture of dichloromethane/methanol/aqueous ammonia, on a Merck 60F254R silica plate).
Workup
- additionare added to the reaction medium
- temperatureheating
- waitis then continued for a further 3 hours at the same temperature
Sources & evidence
- ORD record
- ord-3e39646da6844213bce54d09d8bc38a6
- Source dataset
- uspto-grants-2004_03
- Patent number
- US06699895B2
Reaction notes
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