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

HRID 2229843Notes

Reaction equation

HRID 2229843 reaction equation
[NH2:1][CH: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][CH: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 136174822-Amino-2-(4-methoxyphenyl)ethan-1-ol

Product 1

HCID 18469312N-(tert-butyl)-N'-[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 1.3 g of 2-amino-2-(4-methoxyphenyl)-1-ethanol and 1.46 cm3 of tert-butyl isothiocyanate in 12 cm3 of absolute ethanol for 21 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 40° C., the residue obtained is taken up in 10 cm3 of water. A crystalline precipitate forms, which is filtered off, washed with 3 times 5 cm3 of diethyl ether and dried under reduced pressure (10 Pa) at a temperature in the region of 40° C. 1.32 g of N-(tert-butyl)-N′-[1-(4-methoxyphenyl)-2-hydroxyethyl]thiourea are obtained in the form of a white solid melting at 127° C.

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. filtrationA crystalline precipitate forms, which is filtered off
  3. washwashed with 3 times 5 cm3 of diethyl ether
  4. customdried under reduced pressure (10 Pa) at a temperature in the region of 40° C

Sources & evidence

ORD record
ord-7afdcc919ee04ab1a6dbde75677be8e4
Source dataset
uspto-grants-2002_07
Patent number
US06420566B2

Reaction notes

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