Malonic Acid → HCID 19956411, compound

HRID 1779556Notes

Reaction equation

HRID 1779556 reaction equation
[C:1]([N:5]1[CH2:10][CH2:9][CH2:8][N:7]([CH2:11]/[CH:12]=[CH:13]/[CH2:14][N:15]2[CH2:20][CH2:19][CH2:18][N:17]([C:21](=[O:24])[CH2:22][CH3:23])C2)C1)(=[O:4])[CH2:2][CH3:3].N1C=CC=CC=1.C(O)(=O)CC(O)=O>CO>[C:1]([NH:5][CH2:10][CH2:9][CH2:8][NH:7][CH2:11]/[CH:12]=[CH:13]/[CH2:14][NH:15][CH2:20][CH2:19][CH2:18][NH:17][C:21](=[O:24])[CH2:22][CH3:23])(=[O:4])[CH2:2][CH3:3]

Participants

5

Reactant 3

HCID 867Malonic AcidHCID 1049PyridineHCID 19956381HCID 19956381, compound

Product 1

HCID 19956411HCID 19956411, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of 1.84 g (0.005468mmol) of (E)-1,4-bis(3-propionylhexahydro-pyrimidin-1-yl)but-2-ene (Example 17b), 44 ml of methanol, 2.74 ml (0.03405 mol) of pyridine and 4.11 g (0.03949 mol) of malonic acid is heated for 2 h under reflux and is then concentrated by evaporation in vacuo. 10 ml of 30% sodium hydroxide solution are added to the oily residue, the mixture is extracted thoroughly with ethyl acetate, the combined ethyl acetate extracts are dried over anhydrous sodium sulfate, and the resulting product is concentrated by evaporation in vacuo to a volume of about 25 ml. The crystalline precipitate that forms is filtered off and, for purification purposes, is recrystallised from acetonitrile. The resulting title compound melts at 82°-84° C.

Workup

  1. temperatureis heated for 2 h
  2. temperatureunder reflux
  3. concentrationis then concentrated by evaporation in vacuo
  4. addition10 ml of 30% sodium hydroxide solution are added to the oily residue
  5. extractionthe mixture is extracted thoroughly with ethyl acetate
  6. dry with materialthe combined ethyl acetate extracts are dried over anhydrous sodium sulfate
  7. concentrationthe resulting product is concentrated by evaporation in vacuo to a volume of about 25 ml
  8. filtrationThe crystalline precipitate that forms is filtered off and, for purification purposes
  9. customis recrystallised from acetonitrile

Sources & evidence

ORD record
ord-d15fffea4adb4a4586e417a9dbeebf1c
Source dataset
uspto-grants-1997_05
Patent number
US05627215

Reaction notes

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