Ethyl isothiocyanatoformate → HCID 90016559, compound

HRID 1054948Notes

Reaction equation

HRID 1054948 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][N:5]=[C:4]([NH2:8])[CH:3]=1.[C:9]([N:14]=[C:15]=[S:16])(=[O:13])[O:10][CH2:11][CH3:12]>O1CCOCC1.C(OCC)(=O)C>[CH2:11]([O:10][C:9]([NH:14][C:15]([NH:8][C:4]1[CH:3]=[C:2]([Cl:1])[CH:7]=[CH:6][N:5]=1)=[S:16])=[O:13])[CH3:12]

Participants

5

Reactant 2

HCID 85320Ethyl isothiocyanatoformateHCID 5818662-Amino-4-chloropyridine

Product 1

HCID 90016559HCID 90016559, compoundYield 92.1%

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
25 °C

Procedure

To a solution of 4-chloropyridin-2-amine (2.16 g, 16.8 mmol, Eq: 1.00) in dioxane (70 ml) was added O-ethyl carbonisothiocyanatidate (2.2 g, 1.9 ml, 16.8 mmol, Eq: 1.00) at 25° C. The resulting mixture was stirred for 2 hours at 25° C. The mixture was diluted with ethyl acetate and washed with water and brine, the organic layer was separated, dried over magnesium sulfate, filtrated and evaporated affording 1-ethoxycarbonyl-3-(4-chloro-pyridin-2-yl)-thiourea (4.02 g/92.1%) as a green waxy solid. MS: m/e=257.9 (M−H+)

Workup

  1. washwashed with water and brine
  2. customthe organic layer was separated
  3. dry with materialdried over magnesium sulfate
  4. filtrationfiltrated
  5. customevaporated

Sources & evidence

ORD record
ord-36da59e1646249ebb7c96e13cc0c2d20
Source dataset
uspto-grants-2016_07
Patent number
US09394311B2

Reaction notes

Loading…