Butanoic acid, 2-(ethoxymethylene)-3-oxo-, ethyl ester → HCID 12194769, compound

HRID 917384

Reaction equation

HRID 917384 reaction equation
Cl.[C:2]1([CH2:8][C:9]([NH2:11])=[NH:10])[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:12]([C:15](=[CH:21]OCC)[C:16]([O:18][CH2:19][CH3:20])=[O:17])(=O)[CH3:13].C([O-])(=O)C.[Na+]>CN(C)C=O>[CH2:8]([C:9]1[N:11]=[C:12]([CH3:13])[C:15]([C:16]([O:18][CH2:19][CH3:20])=[O:17])=[CH:21][N:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 97734Butanoic acid, 2-(ethoxymethylene)-3-oxo-, ethyl esterHCID 517045Sodium AcetateHCID 124155142-Phenylethanimidamide hydrochloride

Product 1

HCID 12194769HCID 12194769, compoundYield 89%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

To 100 ml of N,N-dimethylformamide, 17.1 g (100 mmol) of 2-phenylacetoamidine hydrochloric acid salt, synthesized in accordance with a method described in “Tetrahedron”, page 887 (1984), 18.6 g (100 mmol) of ethyl 2-acetyl-3-ethoxyacrylate and 9.0 g (110 mmol) of sodium acetate were suspended, followed by stirring at 100° C. for 3 hours. The reaction liquid was cooled and then poured into ice water, and extracting with diethyl ether. The organic layer was washed with water and a saturated saline solution in this order, followed by drying over anhydrous magnesium sulfate and concentrating under reduced pressure to obtain 22.8 g (yield: 89%) of ethyl 2-benzyl-4-methylpyrimidine-5-carboxylate.

Workup

  1. customThe reaction liquid
  2. temperaturewas cooled
  3. extractionextracting with diethyl ether
  4. washThe organic layer was washed with water
  5. dry with materialby drying over anhydrous magnesium sulfate
  6. concentrationconcentrating under reduced pressure

Sources & evidence

ORD record
ord-22aa77e03b3042448a53c53288fa8fe5
Source dataset
uspto-grants-2007_09
Patent number
US07273878B2

Linked notes

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