Acetic Acid → HCID 178431765, compound

HRID 1094228Notes

Reaction equation

HRID 1094228 reaction equation
[CH2:1]([OH:3])[CH3:2].C[CH2:5][O-:6].[Na+].[CH3:8][C:9]([C:12]([NH2:14])=[NH:13])([CH3:11])[CH3:10].Cl.O.[C:17](O)(=O)C>>[C:9]([C:12]1[N:14]=[C:1]([OH:3])[C:2]([CH3:17])=[C:5]([OH:6])[N:13]=1)([CH3:11])([CH3:10])[CH3:8]

Participants

6

Reactant 5

HCID 176Acetic AcidHCID 702Ethanol2×HCID 962WaterHCID 2723922Sodium ethoxideHCID 2781880Propanimidamide, 2,2-dimethyl-, hydrochloride (1:1)

Product 1

HCID 178431765HCID 178431765, compound

Conditions

Temperature
0 °C

Procedure

A single-necked flask containing 80 ml of ethanol is cooled down to 0° C. by an ice bath, 4 g (55.6 mmoles) of sodium ethylate and 3.8 g (27.8 mmoles) of tert-butylcarbamidine hydrochloride are added. The reaction mixture is left to return to ambient temperature, then 5 ml (27.8 mmoles) of diethyl ester methylmalonate is added dropwise. Stirring is maintained at ambient temperature overnight. The ethanol is then condensed under reduced pressure (2 kPa). The crude product obtained is solubilized in a minimum amount of water (approximately 40 ml), then acidified at 0° C. with pure acetic acid until a pH comprised between 4 and 5 is achieved. The white precipitate formed is filtered, rinsed successively with water, ethyl ether and with pentane. Then the white powder obtained is dried over P2O5 under reduced pressure (0.2 kPa). 2.4 g of expected product is obtained.

Workup

  1. waitThe reaction mixture is left
  2. customto return to ambient temperature
  3. temperatureis maintained at ambient temperature overnight
  4. customcondensed under reduced pressure (2 kPa)
  5. customThe crude product obtained
  6. customThe white precipitate formed
  7. filtrationis filtered
  8. washrinsed successively with water, ethyl ether and with pentane
  9. customThen the white powder obtained
  10. dry with materialis dried over P2O5 under reduced pressure (0.2 kPa)

Sources & evidence

ORD record
ord-8402b4292a6a4db5a8bc0be9d9ec9c1a
Source dataset
uspto-grants-2012_03
Patent number
US08133896B2

Reaction notes

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