Acetic Acid → HCID 12535811, compound

HRID 2082737Notes

Reaction equation

HRID 2082737 reaction equation
Cl.[CH2:2]([S:4][C:5]1[CH:13]=[CH:12][CH:11]=[CH:10][C:6]=1[C:7]([NH2:9])=[NH:8])[CH3:3].[Na].C([O:17][CH:18]=[C:19]([C:25](OCC)=O)[C:20]([O:22][CH2:23][CH3:24])=[O:21])C.C(O)(=O)C>C(O)C>[O:17]=[C:18]1[NH:9][C:7]([C:6]2[CH:10]=[CH:11][CH:12]=[CH:13][C:5]=2[S:4][CH2:2][CH3:3])=[N:8][CH:25]=[C:19]1[C:20]([O:22][CH2:23][CH3:24])=[O:21]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 6871Diethyl (ethoxymethylene)malonateHCID 5360545SodiumHCID 20360326HCID 20360326, compound

Product 1

HCID 12535811HCID 12535811, compoundYield 67%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

2-Ethylthiobenzamidine hydrochloride (2.12 g., 10.0 mmoles) was added to a cooled (ice-water) solution of sodium (0.46 g., 20 mg.-atoms) in ethanol (12 ml.). To this mixture was added a solution of diethyl ethoxymethylenemalonate (2.16 g., 10.0 mmoles) in ethanol (4 ml.). The mixture was heated under reflux for 3.5 hours. The cooled mixture was poured into ice-water (400 ml.) and acidified to pH 6 with glacial acetic acid. The precipitate was collected and recrystallized from acetonitrile to give the title compound (2.04 g., 64.6%), m.p. 117°-120°.

Workup

  1. temperatureThe mixture was heated
  2. temperatureunder reflux for 3.5 hours
  3. customThe precipitate was collected
  4. customrecrystallized from acetonitrile

Sources & evidence

ORD record
ord-a6130121747b45d78055f15f265ce7d3
Source dataset
uspto-grants-1978_04
Patent number
US04082751

Reaction notes

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