tert-Butyl isothiocyanate → N-(tert-butyl)-N'-[(1R)-1-butyl-2-hydroxyethyl]thiourea

HRID 1280643

Reaction equation

HRID 1280643 reaction equation
[NH2:1][C@H:2]([CH2:5][CH2:6][CH2:7][CH3:8])[CH2:3][OH:4].[C:9]([N:13]=[C:14]=[S:15])([CH3:12])([CH3:11])[CH3:10]>C(O)C>[C:9]([NH:13][C:14]([NH:1][C@H:2]([CH2:5][CH2:6][CH2:7][CH3:8])[CH2:3][OH:4])=[S:15])([CH3:12])([CH3:11])[CH3:10]

Participants

4

Reactant 2

HCID 11544tert-Butyl isothiocyanateHCID 6994402(R)-2-Aminohexan-1-ol

Product 1

HCID 86584433N-(tert-butyl)-N'-[(1R)-1-butyl-2-hydroxyethyl]thiourea

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
20 °C

Procedure

The process is performed as in Example 2, starting with 1.14 g of (2R)-2-amino-2-butyl-1-ethanol and 1.36 cm3 of tert-butyl isothiocyanate in 15 cm3 of ethanol, with stirring for 18 hours at a temperature in the region of 20° C. and then for 3 hours in the region of 60° C. After concentration of the reaction medium under reduced pressure (5 kPa) at a temperature in the region of 40° C. 2.38 g of N-(tert-butyl)-N′-[(1R)-1-butyl-2-hydroxyethyl]thiourea are obtained in the form of a yellow oil. Infrared spectrum (CH2Cl2): 3620; 4430; 4410; 2960; 1560; 1500; 1395; 1375 and 1205 cm−.

Workup

  1. waitfor 3 hours in the region of 60° C
  2. customin the region of 40° C

Sources & evidence

ORD record
ord-b44fe8087a774d4e8311a5d17e1c76e2
Source dataset
uspto-grants-2002_09
Patent number
US06451821B1

Linked notes

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