Water → Thiourea, N-ethyl-N'-phenyl-

HRID 1809958Notes

Reaction equation

HRID 1809958 reaction equation
[CH2:1]([N:3]=[C:4]=[S:5])[CH3:2].[NH2:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.O>C(#N)C>[CH2:1]([NH:3][C:4]([NH:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)=[S:5])[CH3:2]

Participants

5

Reactant 3

HCID 962WaterHCID 6115AnilineHCID 10966Ethyl isothiocyanate

Product 1

HCID 2063659Thiourea, N-ethyl-N'-phenyl-

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A solution of ethyl isothiocyanate (1-1) (652 mg, 7.5 mmol) and aniline (1-2) (465 mg, 5.0 mmol) in acetonitrile (5 mL) is heated to 80° C. for 14 hours. After cooling to room temperature, the mixture is poured into water (50 mL) and extracted with ethyl acetate (EtOAc) (3×50 mL). The combined organic layers are washed with brine and dried using MgSO4. The drying agents are removed by filtration and the solvent is removed under vacuum. The resulting residue is then purified by flash column chromatography (silica gel, EtOAc/hexane, 0%˜40%) to provide 1-ethyl-3-phenylthiourea (1-3) as a white powder. HPLC-MS calculated for C9H12N2S (M+H+) 181.1. found 181.1.

Workup

  1. extractionextracted with ethyl acetate (EtOAc) (3×50 mL)
  2. washThe combined organic layers are washed with brine
  3. customdried
  4. customThe drying agents are removed by filtration
  5. customthe solvent is removed under vacuum
  6. customThe resulting residue is then purified by flash column chromatography (silica gel, EtOAc/hexane, 0%˜40%)

Sources & evidence

ORD record
ord-c3ffb94089494bfb9ed81382837854a9
Source dataset
uspto-grants-2013_01
Patent number
US08362050B2

Reaction notes

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