Ethyl isothiocyanatoformate → Ethyl {[(5-methoxypyridin-2-yl)amino]carbonothioyl}carbamate

HRID 2095789Notes

Reaction equation

HRID 2095789 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([NH2:9])=[N:7][CH:8]=1.[N:10]([C:13]([O:15][CH2:16][CH3:17])=[O:14])=[C:11]=[S:12]>CS(C)=O.O>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([NH:9][C:11]([NH:10][C:13](=[O:14])[O:15][CH2:16][CH3:17])=[S:12])=[N:7][CH:8]=1

Participants

5

Reactant 2

HCID 85320Ethyl isothiocyanatoformateHCID 113209342-Amino-5-methoxypyridine

Product 1

HCID 58087980Ethyl {[(5-methoxypyridin-2-yl)amino]carbonothioyl}carbamateYield 62.3%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolvent

Procedure

To a solution of 5-methoxypyridin-2-amine (1.05 g, 8.43 mmol) in dimethyl sulfoxide (5 mL) was added ethyl isothiocyanatoformate (1.44 g, 11.0 mmol), and the mixture was stirred for 15 hr. The reaction mixture was diluted with water, and extracted with ethyl acetate (×3). The combined organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate and filtered. The filtrate was concentrated under reduced pressure, and the residue was dried to give the title compound (1.34 g, 62%) as a white solid.

Workup

  1. extractionextracted with ethyl acetate (×3)
  2. washThe combined organic layer was washed with saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. filtrationfiltered
  5. concentrationThe filtrate was concentrated under reduced pressure
  6. customthe residue was dried

Sources & evidence

ORD record
ord-ec62200970e04e2dbe52955ce091687b
Source dataset
uspto-grants-2013_05
Patent number
US08445509B2

Reaction notes

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