2-Nitrothiophene-4-carboxaldehyde → HCID 9924484, compound

HRID 1837111Notes

Reaction equation

HRID 1837111 reaction equation
[NH2:1][C:2]1[N:3]([CH3:8])[O:4][C:5](=[O:7])[CH:6]=1.[N+:9]([C:12]1[S:16][CH:15]=[C:14]([CH:17]=O)[CH:13]=1)([O-:11])=[O: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:17]([C:14]3[CH:13]=[C:12]([N+:9]([O-:11])=[O:10])[S:16][CH:15]=3)[C:6]=2[C:5](=[O:7])[O:4]1

Participants

5

Reactant 3

HCID 1447302-Nitrothiophene-4-carboxaldehydeHCID 3252872H-pyran-3,5(4H,6H)-dioneHCID 234974983-Amino-2-methyl-2,5-dihydro-1,2-oxazol-5-one

Product 1

HCID 9924484HCID 9924484, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

The product from Example 45A (0.086 g, 0.75 mmol), 5-nitro-3-thiophenecarbaldehyde (0.12 g, 0.75 mmol) and 2H-pyran-3,5(4H,6H)-dione (0.085 g, 0.75 mmol) in ethyl alcohol (2 mL) were heated at 80° C. for 2 days in a sealed tube. The reaction mixture was allowed to cool to ambient temperature and was evaporated under reduced pressure. The residue was crystallized from methylene chloride/ethanol to provide the title product. 1H NMR (300 MHz, DMSO-d,) δ 3.23 (s, 3H), 4.1 (q, 2H), 4.53 (s, 2H), 4.88 (s, 1H), 7.7 (d, 1H), 7.92 (d, 1H), 10.8 (s, 1H); MS (ESI) m/z 348 (M−H)−, Anal. Calcd for C14H11N3O6S: C, 48.13; H, 3.15; N, 12.03. Found: C, 47.76; H, 3.25; N, 11.78.

Workup

  1. customwas evaporated under reduced pressure
  2. customThe residue was crystallized from methylene chloride/ethanol

Sources & evidence

ORD record
ord-e58c0b51e3da48638f3ce6c159b24c7a
Source dataset
uspto-grants-2004_08
Patent number
US06780872B2

Reaction notes

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