tert-Butyl isothiocyanate → N-[(2S)-2-hydroxypropyl]-N'-tert-butylthiourea

HRID 47745Notes

Reaction equation

HRID 47745 reaction equation
[NH2:1][CH2:2][C@@H:3]([OH:5])[CH3:4].[C:6]([N:10]=[C:11]=[S:12])([CH3:9])([CH3:8])[CH3:7]>C(O)C.C(OCC)C>[OH:5][C@@H:3]([CH3:4])[CH2:2][NH:1][C:11]([NH:10][C:6]([CH3:9])([CH3:8])[CH3:7])=[S:12]

Participants

5

Reactant 2

HCID 11544tert-Butyl isothiocyanateHCID 7311736(S)-(+)-1-Aminopropan-2-ol

Product 1

HCID 23381537N-[(2S)-2-hydroxypropyl]-N'-tert-butylthioureaYield 93.6%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 3283Diethyl EtherSolvent

Conditions

Temperature
20 °C

Procedure

The process is performed as in Example 1, starting with 5 g of (+)-(S)-1-amino-2-propanol and 8.43 g of tert-butyl isothiocyanate in 60 cm3 of ethanol. After stirring the reaction medium for 5 hours at a temperature in the region of 20° C. and then concentration under reduced pressure (5 kPa) at a temperature in the region of 50° C., the white solid obtained is taken up in diethyl ether. The suspension is again concentrated under the same conditions as above. 11.86 g of N-[(2S)-2-hydroxypropyl]-N′-tert-butylthiourea are obtained in the form of a white solid melting at 106° C.

Workup

  1. concentrationconcentration under reduced pressure (5 kPa) at a temperature in the region of 50° C.
  2. customthe white solid obtained
  3. concentrationThe suspension is again concentrated under the same conditions as above

Sources & evidence

ORD record
ord-7e98585b952d43d2904d99276cac5898
Source dataset
uspto-grants-2004_03
Patent number
US06699895B2

Reaction notes

Loading…