Ethyl oxamate → HCID 20377474, compound

HRID 2052250Notes

Reaction equation

HRID 2052250 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-c4cf1bcf98754f76a205cbe3beac7f4a
Source dataset
uspto-grants-1980_01
Patent number
US04183925

Reaction notes

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