Methanol → HCID 178518555, compound

HRID 2396677Notes

Reaction equation

HRID 2396677 reaction equation
C(OC([NH:6][C:7]([NH:9][C:10]1[C:11]([C:16]([O:18]C)=O)=[N:12][CH:13]=[CH:14][CH:15]=1)=[S:8])=O)C.C[O-].[Na+].CO>C(O)C>[OH:18][C:16]1[C:11]2[N:12]=[CH:13][CH:14]=[CH:15][C:10]=2[N:9]=[C:7]([SH:8])[N:6]=1

Participants

5

Reactant 3

HCID 887MethanolHCID 10942334Sodium MethoxideHCID 18985857HCID 18985857, compound

Product 1

HCID 178518555HCID 178518555, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 37.2 g (0.13 mol) of N-ethoxycarbonyl-N'-(2-methoxycarbonyl-3-pyridinyl)thiourea and 33 mL of 25 percent sodium methoxide in methanol (0.14 mol) in 500 mL of absolute ethanol was heated to reflux with stirring. A solid began to form after about 5 min and after 1 hour heating was discontinued and the volatile components were removed by evaporation under reduced pressure. The residue was diluted with water, acidified with acetic acid, and filtered to recover the solids. The solids were extracted on the filter with ether and then with acetone to obtain a fine powder that was difficult to filter. This was extracted with ether again (added while some acetone was still present) and, finally, with hexane to obtain the 23.3 g of title compound as a more easily filtered pale yellow granular solid melting above 300° C.

Workup

  1. temperaturewas heated
  2. temperatureto reflux
  3. customto form after about 5 min and after 1 hour
  4. temperatureheating
  5. customthe volatile components were removed by evaporation under reduced pressure
  6. additionThe residue was diluted with water
  7. filtrationfiltered
  8. customto recover the solids
  9. extractionThe solids were extracted on the
  10. filtrationfilter with ether
  11. customwith acetone to obtain a fine powder that
  12. filtrationto filter
  13. extractionThis was extracted with ether again (
  14. additionadded while some acetone

Sources & evidence

ORD record
ord-d343d310643d4b37b53fe7d2f8e8d037
Source dataset
uspto-grants-1996_02
Patent number
US05494887

Reaction notes

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