tert-Butyl isothiocyanate → N-(tert-butyl)-N'-[(1S)-1-cyclohexylmethyl-2-hydroxyethyl]thiourea
Reaction equation
[NH2:1][C@@H:2]([CH2:5][CH:6]1[CH2:11][CH2:10][CH2:9][CH2:8][CH2:7]1)[CH2:3][OH:4].[C:12]([N:16]=[C:17]=[S:18])([CH3:15])([CH3:14])[CH3:13]>C(O)C>[C:12]([NH:16][C:17]([NH:1][C@@H:2]([CH2:5][CH:6]1[CH2:11][CH2:10][CH2:9][CH2:8][CH2:7]1)[CH2:3][OH:4])=[S:18])([CH3:15])([CH3:14])[CH3:13]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 20 °C
Procedure
The process is performed as in Example 3, starting with 8.1 g of (+)-(2S)-2-amino-3-cyclohexyl-1-propanol and 9.8 cm3 of tert-butyl isothiocyanate in 79 cm3 of ethanol. The reaction medium is stirred for 72 hours at a temperature in the region of 20° C. After concentration of the reaction mass under reduced pressure (5 kPa) at a temperature in the region of 50° C., the oil obtained is taken up in 110 cm3 of cold petroleum ether. The crystals are filtered off and dried under reduced pressure (10 Pa) at a temperature in the region of 60° C. 11.1 g of N-(tert-butyl)-N′-[(1S)-1-cyclohexylmethyl-2-hydroxyethyl]thiourea are obtained in the form of a white solid melting at 97° C.
Workup
- customAfter concentration of the reaction mass under reduced pressure (5 kPa) at a temperature in the region of 50° C., the oil obtained
- filtrationThe crystals are filtered off
- customdried under reduced pressure (10 Pa) at a temperature in the region of 60° C
Sources & evidence
- ORD record
- ord-b5644432ac1448a9b92abb0f03571ed0
- Source dataset
- uspto-grants-2004_03
- Patent number
- US06699895B2
Reaction notes
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