1-Propanol → HCID 53648704, compound

HRID 843667Notes

Reaction equation

HRID 843667 reaction equation
[CH3:1][O:2][C:3]([C:5]1[C:9](=[O:10])[CH2:8][S:7][C:6]=1[NH:11][C:12]([N:14]([CH3:16])[CH3:15])=[O:13])=[O:4].OS(O)(=O)=O.[CH2:22](O)[CH2:23][CH3:24]>>[CH3:1][O:2][C:3]([C:5]1[C:9]([O:10][CH2:22][CH2:23][CH3:24])=[CH:8][S:7][C:6]=1[NH:11][C:12]([N:14]([CH3:15])[CH3:16])=[O:13])=[O:4]

Participants

4

Reactant 3

HCID 10311-PropanolHCID 1118Sulfuric AcidHCID 178498856HCID 178498856, compound

Product 1

HCID 53648704HCID 53648704, compoundYield 53%

Procedure

A solution of 2-(3,3-Dimethyl-ureido)-4-oxo-4,5-dihydro-thiophene-3-carboxylic acid methyl ester (50 mg, 0.205 mmol) in n-propanol (5 mL) was treated with H2SO4 (5 microliters) and stirred at ambient temperature for 12 hours. Little reaction was observed so the temperature was increased to 100° C. Little reaction was observed after 2 hours so four angstrom seives were added and the reaction continued at 100° C. for two additional hours at which point sufficient product was observed. The mixture was then concentrated and the residue purified via radial chromatography on a 4 mm plate using hexanes/ethyl acetate (1/1) to afford the title compound as a white solid (31 mg, 0.108 mmol, 53%) 1H NMR (CDCL3, 400 MHz) 1.03 (t, 3H, J=7.3 Hz), 1.78-1.84 (m, 2H), 3.06 (s, 6H), 3.84-3.89 (m, 5H), 5.51 (s, 1H), 11.08 (s, 1H).

Workup

  1. customLittle reaction
  2. temperaturewas increased to 100° C
  3. customLittle reaction
  4. waitwas observed after 2 hours
  5. additionso four angstrom seives were added
  6. customcontinued at 100° C. for two additional hours at which point sufficient product
  7. concentrationThe mixture was then concentrated
  8. customthe residue purified via radial chromatography on a 4 mm plate

Sources & evidence

ORD record
ord-e507e86d688b46e9a122ae0c37611709
Source dataset
uspto-grants-2002_04
Patent number
US06380214B1

Reaction notes

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