Thionyl Chloride → HCID 178499502, compound

HRID 1159673Notes

Reaction equation

HRID 1159673 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].[C:15]([CH:18]([CH2:23][C:24]([O:26][CH3:27])=[O:25])[C:19](OC)=[O:20])(=O)[CH3:16].C[O-].[Na+].S(Cl)(Cl)=O>CO.CC(C)=O>[OH:20][C:19]1[C:18]([CH2:23][C:24]([O:26][CH3:27])=[O:25])=[C:15]([CH3:16])[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 24386Thionyl ChlorideHCID 112039Dimethyl acetylsuccinateHCID 10942334Sodium MethoxideHCID 463184212-(4-Nitrophenyl)ethanimidamide hydrochloride

Product 1

HCID 178499502HCID 178499502, compoundYield 38%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 887MethanolSolvent2×

Procedure

A mixture of 2-(4-nitrophenyl)ethanimidamide hydrochloride (0.22 g, 1.0 mmol), dimethyl acetyl-succinate (0.19 g, 1.0 mmol), and sodium methoxide (0.07 g, 1.3 mmol) in MeOH (10 mL) was refluxed for 15 hours. After cooling to room temperature, the separated solids were collected by suction and added to a pre-formed solution of thionyl chloride (0.65 mL, 8.9 mmol) in MeOH (7.5 mL). The resulting mixture was refluxed for 16 hours and then cooled to room temperature. Acetone was added and the precipitated solids were collected by suction, rinsed with acetone and dried under high vacuum for 4 hours to give methyl [4-hydroxy-6-methyl-2-(4-nitrobenzyl)-pyrimidin-5-yl]acetate (0.12 g, 38% yield) as a white solid.

Workup

  1. temperaturewas refluxed for 15 hours
  2. customthe separated solids were collected by suction
  3. temperatureThe resulting mixture was refluxed for 16 hours
  4. temperaturecooled to room temperature
  5. customthe precipitated solids were collected by suction
  6. washrinsed with acetone
  7. customdried under high vacuum for 4 hours

Sources & evidence

ORD record
ord-cd7a38a56bae4a0096049159f478d3c4
Source dataset
uspto-grants-2010_10
Patent number
US07812160B2

Reaction notes

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