tert-Butyl isothiocyanate → HCID 23508190, compound

HRID 1883601Notes

Reaction equation

HRID 1883601 reaction equation
[NH2:1][CH:2]([CH2:5][C:6]1[CH:11]=[CH:10][N:9]=[CH:8][C:7]=1[O:12][CH3:13])[CH2:3][OH:4].[C:14]([N:18]=[C:19]=[S:20])([CH3:17])([CH3:16])[CH3:15]>C(O)C>[C:14]([NH:18][C:19]([NH:1][CH:2]([CH2:5][C:6]1[CH:11]=[CH:10][N:9]=[CH:8][C:7]=1[O:12][CH3:13])[CH2:3][OH:4])=[S:20])([CH3:17])([CH3:16])[CH3:15]

Participants

4

Reactant 2

HCID 11544tert-Butyl isothiocyanate2×HCID 23508187HCID 23508187, compound

Product 1

HCID 23508190HCID 23508190, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
20 °C

Procedure

To a solution of 0.3 g of 2-amino-3-(3-methoxy-pyridin-4-yl)-1-propanol in 50 mL of absolute ethanol, about 0.337 mL of tert-butylisothiocyanate is added then the reaction medium is stirred under an inert atmosphere at a temperature of about 20° C. for 18 hours. About 0.337 mL of tert-butylisothiocyanate is added again and the reaction mixture is heated at a temperature of about 60° C. for 4 hours. After cooling, the reaction medium is concentred under reduced pressure (2 kPa) at a temperature of about de 40° C. The oil obtained is purified by chromatography under argon pressure (50 kPa), in a column of silica gel (particle size 40-63 μm; diameter 4 cm; height 22 cm), eluting with a 20% dichloromethane/methanol/aqueous ammonia mixture (90/10/0.5 by volume) and obtaining fractions of 10 mL. The fractions containing the expected product are collected and concentred under reduced pressure (2 kPa) at a temperature of about 40° C. About 0.4 g of N-(tert-butyl)-N′-[2-hydroxy-1-(3-methoxy-pyridin-4-yl-methyl)ethyl]-thiourea is obtained, under the form of an yellow oil. [Infrared spectrum CH2Cl2: 3620; 3411; 2972; 1614; 1561; 1532; 1400; 1319; 1161; 1041 and 815 cm−1].

Workup

  1. temperaturethe reaction mixture is heated at a temperature of about 60° C. for 4 hours
  2. temperatureAfter cooling
  3. customThe oil obtained
  4. customis purified by chromatography under argon pressure (50 kPa)
  5. washin a column of silica gel (particle size 40-63 μm; diameter 4 cm; height 22 cm), eluting with a 20% dichloromethane/methanol/aqueous ammonia mixture (90/10/0.5 by volume)
  6. customobtaining fractions of 10 mL

Sources & evidence

ORD record
ord-8ef58cc8843346efbf8f54d7f821a00b
Source dataset
uspto-grants-2004_07
Patent number
US06762196B2

Reaction notes

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