Methoxyacetyl chloride → HCID 178494705, compound

HRID 1616528Notes

Reaction equation

HRID 1616528 reaction equation
[CH3:1][O:2][CH2:3][C:4](Cl)=O.[NH2:7][NH:8][C:9]([NH2:11])=[S:10]>N1C=CC=CC=1>[CH3:1][O:2][CH2:3][C:4]1[NH:7][N:8]=[C:9]([SH:10])[N:11]=1

Participants

4

Reactant 2

HCID 96623Methoxyacetyl chlorideHCID 2723789Thiosemicarbazide

Product 1

HCID 178494705HCID 178494705, compoundYield 33%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

Methoxyacetyl chloride (2.82 g; 0.023 mol) was added to a solution (15 ml) of 2.09 g (0.0230 mol) of thiosemicarbazide in pyridine followed by stirring for a whole day and night at room temperature. The reaction solution was concentrated and 10 ml of methanol and 8 ml of a 25 wt % methanolic solution of sodium methoxide were added thereto followed by heating to reflux for a whole day and night. After cooling to room temperature, the solvent was evaporated and concentrated hydrochloric acid was added thereto to acidify. The solid separated out therefrom was filtered, washed with distilled water and dried to give 1.0 g (yield: 33%) of the title compound.

Workup

  1. concentrationThe reaction solution was concentrated
  2. addition10 ml of methanol and 8 ml of a 25 wt % methanolic solution of sodium methoxide were added
  3. temperatureby heating
  4. temperatureto reflux for a whole day and night
  5. temperatureAfter cooling to room temperature
  6. customthe solvent was evaporated
  7. additionconcentrated hydrochloric acid was added
  8. customThe solid separated out
  9. filtrationtherefrom was filtered
  10. washwashed with distilled water
  11. customdried

Sources & evidence

ORD record
ord-8df0e14254c34dd0b53a0904f34fe195
Source dataset
uspto-grants-2014_07
Patent number
US08765789B2

Reaction notes

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