Sulfuric Acid → HCID 16050184, compound

HRID 898127Notes

Reaction equation

HRID 898127 reaction equation
C([O:3][CH:4](OCC)[C:5]1[CH:10]=[C:9]([CH3:11])[N:8]=[C:7]([S:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH3:18])[N:6]=1)C.OS(O)(=O)=O.C([O-])([O-])=O.[Na+].[Na+]>C1COCC1>[CH2:13]([S:12][C:7]1[N:6]=[C:5]([CH:4]=[O:3])[CH:10]=[C:9]([CH3:11])[N:8]=1)[CH2:14][CH2:15][CH2:16][CH2:17][CH3:18]

Participants

5

Reactant 3

HCID 1118Sulfuric AcidHCID 10340Sodium CarbonateHCID 16050161HCID 16050161, compound

Product 1

HCID 16050184HCID 16050184, compoundYield 74%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

4-Diethoxymethyl-2-hexylsulfanyl-6-methyl-pyrimidine(19 g, 60.8 mmol) was dissolved in THF (100 mL) and 4 N aqueous H2SO4 (100 mL) and heated at 50° C. for 33 h. Poured in cold 10% Na2CO3 solution (400 mL) and extracted with ethyl acetate and a sat. solution of NaCl. The crude oil was purified by silica gel chromatography with a heptane/DCM gradient of 100:0 to 67:33. One obtained 10.7 g (74%) of a yellow oil.

Workup

  1. extractionextracted with ethyl acetate
  2. customThe crude oil was purified by silica gel chromatography with a heptane/DCM gradient of 100:0 to 67:33

Sources & evidence

ORD record
ord-12cd4769e61243bbb6ce182511a8e4f3
Source dataset
uspto-grants-2008_04
Patent number
US07351700B2

Reaction notes

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