tert-Butyl isothiocyanate → N-(tert-butyl)-N'-[(1R)-1-(4-methoxyphenyl)-2-hydroxyethyl]thiourea

HRID 2229846Notes

Reaction equation

HRID 2229846 reaction equation
[NH2:1][C@H:2]([C:5]1[CH:10]=[CH:9][C:8]([O:11][CH3:12])=[CH:7][CH:6]=1)[CH2:3][OH:4].[C:13]([N:17]=[C:18]=[S:19])([CH3:16])([CH3:15])[CH3:14]>C(O)C.O>[C:13]([NH:17][C:18]([NH:1][C@H:2]([C:5]1[CH:10]=[CH:9][C:8]([O:11][CH3:12])=[CH:7][CH:6]=1)[CH2:3][OH:4])=[S:19])([CH3:16])([CH3:15])[CH3:14]

Participants

5

Reactant 2

HCID 11544tert-Butyl isothiocyanateHCID 10866717(R)-2-Amino-2-(4-methoxyphenyl)ethanol

Product 1

HCID 86584347N-(tert-butyl)-N'-[(1R)-1-(4-methoxyphenyl)-2-hydroxyethyl]thiourea

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

The process is performed under the conditions of Example 1, starting with 5.78 g of (2R)-2-amino-2-(4-methoxyphenyl)-1-ethanol and 6.48 cm3 of tert-butyl isothiocyanate in 73 cm3 of ethanol for 17 h 30 minutes at a temperature in the region of 20° C. The reaction mass is evaporated under reduced pressure (5 kPa) at a temperature in the region of 40° C. and the solid residue obtained is then ground in 45 cm3 of water, filtered and washed with twice 20 cm3 of water and twice 25 cm3 of diethyl ether. The crystals are dried in an oven under reduced pressure (10 Pa) at a temperature in the region of 45° C. 4.9 g of N-(tert-butyl)-N′-[(1R)-1-(4-methoxyphenyl)2-hydroxyethyl]-thiourea are obtained in the form of a white solid. (Rf=0.60 in ethyl acetate, on a Merck 60F254R silica plate).

Workup

  1. customThe reaction mass is evaporated under reduced pressure (5 kPa) at a temperature in the region of 40° C.
  2. customthe solid residue obtained
  3. filtrationfiltered
  4. washwashed with twice 20 cm3 of water and twice 25 cm3 of diethyl ether
  5. customThe crystals are dried in an oven under reduced pressure (10 Pa) at a temperature in the region of 45° C

Sources & evidence

ORD record
ord-2923796e8e0348578d4a6e931c0ef928
Source dataset
uspto-grants-2002_07
Patent number
US06420566B2

Reaction notes

Loading…