Water → HCID 726326, compound

HRID 1809961Notes

Reaction equation

HRID 1809961 reaction equation
[NH2:1][C:2]1[CH:11]=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[CH:4][CH:3]=1.[CH2:12]([N:14]=[C:15]=[S:16])[CH3:13].O>C(#N)C>[CH2:12]([NH:14][C:15](=[S:16])[NH:1][C:2]1[CH:3]=[CH:4][C:5]([C:6]([O:8][CH3:9])=[O:7])=[CH:10][CH:11]=1)[CH3:13]

Participants

5

Reactant 3

HCID 962WaterHCID 10966Ethyl isothiocyanateHCID 12082Methyl 4-aminobenzoate

Product 1

HCID 726326HCID 726326, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of methyl 4-aminobenzoate (2-2) (30.2 mg, 0.20 mmol) in anhydrous acetonitrile (0.4 mL) is added ethyl isothiocyanate (2-1) (17.52 μL, 0.20 mmol) and the reaction mixture is heated at 80° C. overnight. 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 methyl 4-(3-ethylthioureido)benzoate (2-3).

Workup

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

Sources & evidence

ORD record
ord-87e1fef935c8443aaed448f76089c6aa
Source dataset
uspto-grants-2013_01
Patent number
US08362050B2

Reaction notes

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