Hexane → N-(6-Chloro-3-methoxy-2-pyridinyl)-N'-carboethoxythiourea

HRID 1940927Notes

Reaction equation

HRID 1940927 reaction equation
[CH2:1]([O:3][C:4]([N:6]=[C:7]=[S:8])=[O:5])[CH3:2].[NH2:9][C:10]1[C:15]([O:16][CH3:17])=[CH:14][CH:13]=[C:12]([Cl:18])[N:11]=1.CCCCCC>C(Cl)(Cl)Cl>[Cl:18][C:12]1[N:11]=[C:10]([NH:9][C:7]([NH:6][C:4]([O:3][CH2:1][CH3:2])=[O:5])=[S:8])[C:15]([O:16][CH3:17])=[CH:14][CH:13]=1

Participants

5

Reactant 3

HCID 8058HexaneHCID 85320Ethyl isothiocyanatoformateHCID 214643776-Chloro-3-methoxypyridin-2-amine

Product 1

HCID 21464341N-(6-Chloro-3-methoxy-2-pyridinyl)-N'-carboethoxythioureaYield 90.9%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

Ethoxycarbonyl isothiocyanate (3.7 mL, 4.1 g, 31.5 mmol) was added slowly with stirring to a solution of 2-amino-6-chloro-3-methoxypyridine (5.0 g, 31.5 mmol) in chloroform (40 mL) and the mixture was stirred overnight. The solvent was removed by evaporation and the residue obtained was mixed with hexane. The resulting slurry was filtered and the solids collected were washed with a small amount of ether and dried to obtain 8.3 g of the title compound as a man powder melting at 184°-185° C. with decomposition.

Workup

  1. customThe solvent was removed by evaporation
  2. customthe residue obtained
  3. filtrationThe resulting slurry was filtered
  4. customthe solids collected
  5. washwere washed with a small amount of ether
  6. customdried

Sources & evidence

ORD record
ord-b5086040948c4118893ce8615ca37adf
Source dataset
uspto-grants-1997_12
Patent number
US05700940

Reaction notes

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