tert-Butyl isothiocyanate → N-(tert-butyl)-N'-[2-hydroxy-1-(3-bromophenyl)ethyl]thiourea

HRID 2229840Notes

Reaction equation

HRID 2229840 reaction equation
[NH2:1][CH:2]([C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([Br:11])[CH:6]=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][CH:2]([C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([Br:11])[CH:6]=1)[CH2:3][OH:4])=[S:18])([CH3:15])([CH3:14])[CH3:13]

Participants

4

Reactant 2

HCID 11544tert-Butyl isothiocyanateHCID 221450012-Amino-2-(3-bromophenyl)ethanol

Product 1

HCID 11232800N-(tert-butyl)-N'-[2-hydroxy-1-(3-bromophenyl)ethyl]thiourea

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 3.54 g of 2-amino-2-(3-bromophenyl)-1-ethanol, in 20 cm3 of ethanol containing 0.18 cm3 of tert-butyl isothiocyanate is stirred at a temperature in the region of 20° C. for 5 hours. After concentration of the reaction mass under reduced pressure (5 kPa) at a temperature in the region of 40° C., the residue obtained is taken up in 25 cm3 of petroleum ether. The resulting crystals are spin-filtered, washed with twice 25 cm3 of petroleum ether and then dried under reduced pressure (5 kPa) at a temperature in the region of 20° C. 4 g of N-(tert-butyl)-N′-[2-hydroxy-1-(3-bromophenyl)ethyl]thiourea are obtained in the form of a white solid (Rf=0.68 in a 40/5/0.5 by volume dichloromethane/methanol/aqueous ammonia mixture, on a Merck 60F254R silica plate)

Workup

  1. customAfter concentration of the reaction mass under reduced pressure (5 kPa) at a temperature in the region of 40° C., the residue obtained
  2. filtrationThe resulting crystals are spin-filtered
  3. washwashed with twice 25 cm3 of petroleum ether
  4. customdried under reduced pressure (5 kPa) at a temperature in the region of 20° C

Sources & evidence

ORD record
ord-5f705d2c8f8146f685d39e06775d57cb
Source dataset
uspto-grants-2002_07
Patent number
US06420566B2

Reaction notes

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