Acetic Acid → HCID 178499546, compound

HRID 2353321Notes

Reaction equation

HRID 2353321 reaction equation
Cl.[N+:2]([C:5]1[CH:10]=[CH:9][C:8]([CH2:11][C:12](=[NH:14])[NH2:13])=[CH:7][CH:6]=1)([O-:4])=[O:3].[CH:15]([CH:17]([CH2:23][C:24]([O:26][CH2:27]C)=[O:25])[C:18](OCC)=O)=[O:16].C[O-].[Na+].C(O)(=O)C>CO.O>[OH:16][C:15]1[C:17]([CH2:23][C:24]([O:26][CH3:27])=[O:25])=[CH:18][N:13]=[C:12]([CH2:11][C:8]2[CH:7]=[CH:6][C:5]([N+:2]([O-:4])=[O:3])=[CH:10][CH:9]=2)[N:14]=1

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 2315001,4-Diethyl 2-formylbutanedioateHCID 10942334Sodium MethoxideHCID 463184212-(4-Nitrophenyl)ethanimidamide hydrochloride

Product 1

HCID 178499546HCID 178499546, compoundYield 64%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Conditions

Temperature
90 °C

Procedure

To a mixture of 2-(4-nitrophenyl)ethanimidamide hydrochloride (6.06 g, 28.12 mmol) and diethyl 2-formylsuccinate (6.54 g, 32.34 mmol) in methanol (100 mL) was added sodium methoxide (28% in methanol, 11.2 mL, 56.25 mmol) at room temperature, and the reaction mixture was stirred at 90° C. overnight. After the cooling to room temperature, the reaction was quenched with acetic acid (3.38 mL, 59.06 mmol) and water (100 mL) was added to. The resulting precipitates were collected by filtration and washed with water and acetone/diisopropyl ether (3/2) to give methyl [4-hydroxy-2-(4-nitrobenzyl)pyrimidin-5-yl]acetate (5.41 g, 64%) as brown solid.

Workup

  1. additionwas added to
  2. customThe resulting precipitates
  3. filtrationwere collected by filtration
  4. washwashed with water and acetone/diisopropyl ether (3/2)

Sources & evidence

ORD record
ord-f7e52b0c515e48c8921da8b58b33eabb
Source dataset
uspto-grants-2010_07
Patent number
US07750014B2

Reaction notes

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