Water → HCID 178441628, compound

HRID 970083Notes

Reaction equation

HRID 970083 reaction equation
[C:1]([NH2:7])(=[NH:6])[CH2:2][CH2:3][CH2:4][CH3:5].[C:8]([CH:11]([CH2:17][C:18]([O:20][CH2:21][CH3:22])=[O:19])[C:12](OCC)=[O:13])(=O)[CH3:9].[OH-].[K+].O>CO>[CH2:2]([C:1]1[N:7]=[C:12]([OH:13])[C:11]([CH2:17][C:18]([O:20][CH2:21][CH3:22])=[O:19])=[C:8]([CH3:9])[N:6]=1)[CH2:3][CH2:4][CH3:5]

Participants

6

Reactant 4

HCID 962WaterHCID 14797Potassium HydroxideHCID 66197Butanedioic acid, 2-acetyl-, 1,4-diethyl esterHCID 4097830Pentanimidamide

Product 1

HCID 178441628HCID 178441628, compoundYield 82.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

1.41 kg of valeroamidine and 1.41 kg of diethyl acetylsuccinate were dissolved in 4.5 L of methanol and 1.16 kg of potassium hydroxide was added thereto. The mixture was stirred for 15 hours at room temperature, and then 14 L of water was added while stirring. The obtained solid was filtered, dried, and dissolved in 6 L of ethanol. Then, 840 g of thionyl chloride was added by drop for 2 hours and stirred for 12 hours at 60° C. To this mixture was added a solution of 1.22 kg of sodium bicarbonate in 15 L of water and the produced solid was filtered and dried to obtain 1.35 kg (47.8% yield) of the titled compound.

Workup

  1. stirringwhile stirring
  2. filtrationThe obtained solid was filtered
  3. customdried
  4. dissolutiondissolved in 6 L of ethanol
  5. additionThen, 840 g of thionyl chloride was added by drop for 2 hours
  6. stirringstirred for 12 hours at 60° C
  7. additionTo this mixture was added a solution of 1.22 kg of sodium bicarbonate in 15 L of water
  8. filtrationthe produced solid was filtered
  9. customdried

Sources & evidence

ORD record
ord-150e2b3afe85494e9dbf61464f7bd5ca
Source dataset
uspto-grants-2007_12
Patent number
US07309788B2

Reaction notes

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