Ethyl isothiocyanatoformate → HCID 57643101, compound

HRID 1802146Notes

Reaction equation

HRID 1802146 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][N:5]=[C:4]([NH2:8])[CH:3]=1.[CH2:9]([O:11][C:12]([N:14]=[C:15]=[S:16])=[O:13])[CH3:10]>O1CCOCC1>[CH2:9]([O:11][C:12]([NH:14][C:15]([NH:8][C:4]1[CH:3]=[C:2]([Br:1])[CH:7]=[CH:6][N:5]=1)=[S:16])=[O:13])[CH3:10]

Participants

4

Reactant 2

HCID 85320Ethyl isothiocyanatoformateHCID 6932822-Amino-4-bromopyridine

Product 1

HCID 57643101HCID 57643101, compoundYield 95%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
25 °C

Procedure

To a solution of 4-bromopyridin-2-amine (10.4 g, 60.1 mmol) in dioxane (242 ml) is added ethoxycarbonyl isothiocyanate (7.88 g, 6.8 ml, 60.1 mmol) at 25° C. The resulting mixture is stirred for 4 hours at 25° C. The solvent is evaporated, the solid yellow residue diluted with ethyl acetate and washed with water and brine. The organic layer is separated, dried over magnesium sulfate and the solvent is removed in vacuo affording 1-ethoxycarbonyl-3-(4-bromo-pyridin-2-yl)-thiourea (17.37 g, 95%) as a yellow solid. mp.: 107-110° C. MS: m/z=304.0, 305.9 (M+H+).

Workup

  1. customThe solvent is evaporated
  2. additionthe solid yellow residue diluted with ethyl acetate
  3. washwashed with water and brine
  4. customThe organic layer is separated
  5. dry with materialdried over magnesium sulfate
  6. customthe solvent is removed in vacuo

Sources & evidence

ORD record
ord-c39dcad35cdd4f38a584371c947837d0
Source dataset
uspto-grants-2013_01
Patent number
US08349824B2

Reaction notes

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