Acetic Acid → HCID 178523102, compound

HRID 2072677

Reaction equation

HRID 2072677 reaction equation
[Na].[C:2]([NH2:8])(=[O:7])[CH2:3][C:4]([NH2:6])=[O:5].C(O[C:12](=O)[CH2:13][NH:14][C:15](=[O:21])[C:16]1[S:20][CH:19]=[CH:18][CH:17]=1)C.C(O)(=O)C>C(O)C.O>[C:16]1([C:15]([NH:14][CH2:13][C:12]2[N:6]=[C:4]([OH:5])[CH:3]=[C:2]([OH:7])[N:8]=2)=[O:21])[S:20][CH:19]=[CH:18][CH:17]=1

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 7911MalonamideHCID 1720748Ethyl N-(thiophene-2-carbonyl)glycinateHCID 5360545Sodium

Product 1

HCID 178523102HCID 178523102, compoundYield 29.9%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of sodium (1.4 g) in ethanol (120 ml) was added malonamide (3.8 g) and the mixture was heated at 60° C. for an hour under stirring. Then after added N-(2-thenoyl)glycine ethyl ester (8 g), the mixture was refluxed for 6 hours. The mixture was concentrated to give the residue which was diluted with water. The aqueous mixture was neutralized by adding acetic acid to deposit a crystalline product which was collected by filtration and recrystallized from dimethylformamide (DMF) to give the objective product (2.8 g) as colorless crystals, mp 270°-275° C. (decompd.).

Workup

  1. temperaturethe mixture was refluxed for 6 hours
  2. concentrationThe mixture was concentrated
  3. customto give the residue which
  4. filtrationwas collected by filtration
  5. customrecrystallized from dimethylformamide (DMF)

Sources & evidence

ORD record
ord-55e0a80065a640df8af85270c226556e
Source dataset
uspto-grants-1990_04
Patent number
US04914104

Linked notes

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