Ethyl oxamate → HCID 20377474, compound

HRID 614237Notes

Reaction equation

HRID 614237 reaction equation
C[O-].[Na+].[CH3:4][O:5][C:6]1[CH:17]=[CH:16][C:9]([CH2:10][NH:11][C:12](=[S:15])[NH:13][NH2:14])=[CH:8][CH:7]=1.[C:18](OCC)(=[O:22])[C:19]([NH2:21])=[O:20]>CO>[C:18]([NH:14][NH:13][C:12]([NH:11][CH2:10][C:9]1[CH:8]=[CH:7][C:6]([O:5][CH3:4])=[CH:17][CH:16]=1)=[S:15])(=[O:22])[C:19]([NH2:21])=[O:20]

Participants

5

Reactant 3

HCID 69238Ethyl oxamateHCID 7121304-(4-Methoxybenzyl)-3-thiosemicarbazideHCID 10942334Sodium Methoxide

Product 1

HCID 20377474HCID 20377474, compoundYield 91%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Sodium methoxide (5.4 g., 0.1 mole) and 4-(p-methoxybenzyl)thiosemicarbazide (2.1 g., 0.1 mole) were stirred in methanol (200 ml.) for a period of five minutes. Ethyl oxamate (11.7 g., 0.1 mole) was then added to the mixture and the resulting mixture was refluxed for a period of three hours. At this point, most of the solvent was evaporated under reduced pressure, water (200 ml.) was added to the residue and the pH adjusted to 2.0 with dilute hydrochloric acid. The resulting solid was then filtered and subsequently dried in vacuo at 50° C. to yield pure 1-oxamoyl-4-(p-methoxybenzyl)-3-thiosemicarbazide (25.7 g., 91% yield), m.p. 185°-190° C.

Workup

  1. temperaturethe resulting mixture was refluxed for a period of three hours
  2. customAt this point, most of the solvent was evaporated under reduced pressure, water (200 ml.)
  3. additionwas added to the residue
  4. filtrationThe resulting solid was then filtered
  5. customsubsequently dried in vacuo at 50° C.

Sources & evidence

ORD record
ord-e74cf124327a4d6182c29a75f43dded9
Source dataset
uspto-grants-1979_03
Patent number
US04144240

Reaction notes

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