Ethylparaben → HCID 58247411, compound

HRID 2359653Notes

Reaction equation

HRID 2359653 reaction equation
[Cl:1][C:2]1[N:7]=[C:6](Cl)[C:5]([N+:9]([O-:11])=[O:10])=[CH:4][N:3]=1.C([O-])(O)=O.[Na+].[CH2:17]([O:19][C:20](=[O:28])[C:21]1[CH:26]=[CH:25][C:24]([OH:27])=[CH:23][CH:22]=1)[CH3:18]>CC(C)=O>[CH2:17]([O:19][C:20](=[O:28])[C:21]1[CH:26]=[CH:25][C:24]([O:27][C:6]2[C:5]([N+:9]([O-:11])=[O:10])=[CH:4][N:3]=[C:2]([Cl:1])[N:7]=2)=[CH:23][CH:22]=1)[CH3:18]

Participants

5

Reactant 3

HCID 8434EthylparabenHCID 516892Sodium BicarbonateHCID 5212662,4-Dichloro-5-nitropyrimidine

Product 1

HCID 58247411HCID 58247411, compound

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent2×

Conditions

Temperature
0 °C

Procedure

To a suspension of Compound 1a (2.0 g; 10.31 mmol) and 0.5N NaHCO3 (20 mL; 10 mmol) in acetone (60 mL) was added a solution of 4-hydroxy-benzoic acid ethyl ester (1.71 g; 10.29 mmol) in acetone (20 mL) dropwise at 0° C. The mixture was stirred at 0° C. for 1 h. The reaction mixture was concentrated under reduced pressure. The resultant residue was extracted with EtOAc (2×20 mL). The organic layer was washed with brine and dried over MgSO4 and concentrated. The crude product was purified by normal phase chromatography (SiO2) to give Compound 16a. 1H NMR (300 MHz, CDCl3): δ 9.20 (s, 1H), 8.20 (d, 2H), 7.25 (d, 2H), 4.45 (q, 2H), 1.4 (t, 3H); MS: m/z 324.1 (M+H)+.

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. extractionThe resultant residue was extracted with EtOAc (2×20 mL)
  3. washThe organic layer was washed with brine
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated
  6. customThe crude product was purified by normal phase chromatography (SiO2)

Sources & evidence

ORD record
ord-bb82d8825d794362808ff161c8e988e0
Source dataset
uspto-grants-2014_04
Patent number
US08685990B2

Reaction notes

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