m-Formylbenzonitrile → HCID 9901742, compound

HRID 1862455Notes

Reaction equation

HRID 1862455 reaction equation
[NH2:1][C:2]1[N:3]([CH3:8])[O:4][C:5](=[O:7])[CH:6]=1.[C:9]([C:11]1[CH:12]=[C:13]([CH:16]=[CH:17][CH:18]=1)[CH:14]=O)#[N:10].[O:19]1[CH2:24][C:23](=O)[CH2:22][C:21](=[O:26])[CH2:20]1>C(O)C>[CH3:8][N:3]1[C:2]2[NH:1][C:23]3[CH2:24][O:19][CH2:20][C:21](=[O:26])[C:22]=3[CH:14]([C:13]3[CH:12]=[C:11]([CH:18]=[CH:17][CH:16]=3)[C:9]#[N:10])[C:6]=2[C:5](=[O:7])[O:4]1

Participants

5

Reactant 3

HCID 90670m-FormylbenzonitrileHCID 3252872H-pyran-3,5(4H,6H)-dioneHCID 234974983-Amino-2-methyl-2,5-dihydro-1,2-oxazol-5-one

Product 1

HCID 9901742HCID 9901742, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

The product from Example 45A (0.085 g, 0.75 mmol), 3-cyanobenzaldehyde (0.14 g, 0.75 mmol) and 2H-pyran-3,5(4H,6H)-dione (0.085 g, 0.75 mmol) were heated in 2 mL of ethanol for 2 days. The resulting mixture was allowed to cool to ambient temperature and filtered to provide the title compound as the filter cake (0.09 g). 1H NMR (300 MHz, DMSO-d6) δ 3.28 (s, 3H), 4.05 (s, 2H), 4.59 (q, 2H), 4.81 (s, 1H), 7.5 (t, 1H), 7.6 (m, 1H), 7.62 (m, 1H), 7.64 (d, 1H), 10.8 (s, 1H); MS (ESI) m/z 322 (M−H)−; Anal. Calcd for C17H13N3O4.0.25H2O: C, 62.48;H, 3.86; N, 12.86. Found: C, 62.55;H, 4.07; N, 12.61.

Workup

  1. filtrationfiltered

Sources & evidence

ORD record
ord-ea54950b9ea142b583de9b62f25a4f49
Source dataset
uspto-grants-2003_03
Patent number
US06538004B2

Reaction notes

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