Benzaldehyde → XR 334

HRID 1458545Notes

Reaction equation

HRID 1458545 reaction equation
C([N:4]1[CH2:9][C:8](=[O:10])[NH:7]/[C:6](=[CH:11]\[C:12]2[CH:17]=[CH:16][C:15]([O:18][CH3:19])=[CH:14][CH:13]=2)/[C:5]1=[O:20])(=O)C.[CH:21](=O)[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1.C(N(CC)CC)C.C(OCC)(=O)C>CN(C=O)C>[CH:21](=[C:9]1/[C:8](=[O:10])[NH:7]/[C:6](=[CH:11]\[C:12]2[CH:13]=[CH:14][C:15]([O:18][CH3:19])=[CH:16][CH:17]=2)/[C:5](=[O:20])[NH:4]/1)\[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1

Participants

6

Reactant 4

HCID 240BenzaldehydeHCID 8471TriethylamineHCID 8857Ethyl AcetateHCID 5392210HCID 5392210, compound

Product 1

HCID 9797139XR 334

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
130 °C

Procedure

A mixture of (3Z)-1-acetyl-3-(4-methoxybenzylidene)-2,5-piperazinedione (9) (1.0 g, 3.6 mmol), benzaldehyde (430 μl, 4.2 mmol) and triethylamine (1.14 ml), 8.2 mmol), in dry DMF (20 ml), was heated at 130° C. for 18 h. The reaction mixture was cooled to room temperature and poured into ethyl acetate (100 ml). A yellow solid precipitated which was filtered off and dried. Yield 360 mg (31%).

Workup

  1. temperatureThe reaction mixture was cooled to room temperature
  2. customA yellow solid precipitated which
  3. filtrationwas filtered off
  4. customdried

Sources & evidence

ORD record
ord-b6ea94baf10a4406b767e769965db8c6
Source dataset
uspto-grants-1998_12
Patent number
US05852018

Reaction notes

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