Acetonitrile → HCID 2794456, compound

HRID 2304563Notes

Reaction equation

HRID 2304563 reaction equation
[CH2:1]([CH:3]([C:7](Cl)=[O:8])[C:4](Cl)=[O:5])[CH3:2].N[CH2:11][C:12]([C:14]1C=CC=C[CH:15]=1)=O.C([N:22]([CH2:25][CH3:26])CC)C.CC[O-:29].[Na+].[C:31](#N)[CH3:32]>>[CH3:2][C:1]1[C:26]2[C:25](=[CH:11][CH:12]=[CH:14][CH:15]=2)[NH:22][C:4](=[O:5])[C:3]=1[C:7]([O:8][CH2:31][CH3:32])=[O:29]

Participants

6

Reactant 5

HCID 6342Acetonitrile2×HCID 8471TriethylamineHCID 11952PhenacylamineHCID 2723922Sodium ethoxideHCID 109209242-Ethylpropanedioyl dichloride

Product 1

HCID 2794456HCID 2794456, compoundYield 84%

Procedure

A solution of ethylmalonyl chloride (12.9 ml, 100 mmol) in anhydrous acetonitrile (30 ml) is added dropwise to a solution of 2-aminoacetophenone (10.5 g, 78 mmol) and triethylamine (13.9 ml, 100 mmol) in anhydrous acetonitrile (110 ml), under argon and at 0° C. The reaction medium is heated up to ambient temperature then treated dropwise and under argon with a solution of sodium ethylate (obtained with 1.8 g, 78 mmol, of sodium in 80 ml of ethanol), then left under agitation for 12 hours at ambient temperature. The reaction mixture is then poured into ice cold water (100 ml) and agitated for two hours, then filtered. The precipitate collected in this way is washed with water, with ethanol and with ether in order to produce 15.2 g (84%) of a white solid.

Workup

  1. filtrationfiltered
  2. customThe precipitate collected in this way
  3. washis washed with water, with ethanol and with ether in order

Sources & evidence

ORD record
ord-94acfff982c3403a873a8081385409de
Source dataset
uspto-grants-2002_08
Patent number
US06436951B1

Reaction notes

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