Ethanol → HCID 9924484, compound

HRID 1862459Notes

Reaction equation

HRID 1862459 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:13][CH:14]=[CH:15][C:16]=1C=O)([O-:11])=[O:10].[O:19]1[CH2:24][C:23](=[O:25])[CH2:22][C:21](=O)[CH2:20]1.[CH2:27](O)C>>[CH3:8][N:3]1[C:2]2[NH:1][C:21]3[CH2:20][O:19][CH2:24][C:23](=[O:25])[C:22]=3[CH:27]([C:15]3[CH:16]=[C:12]([N+:9]([O-:11])=[O:10])[S:13][CH:14]=3)[C:6]=2[C:5](=[O:7])[O:4]1

Participants

5

Reactant 4

HCID 702EthanolHCID 3252872H-pyran-3,5(4H,6H)-dioneHCID 105588712-Nitro-3-thiophenecarboxaldehydeHCID 234974983-Amino-2-methyl-2,5-dihydro-1,2-oxazol-5-one

Product 1

HCID 9924484HCID 9924484, compound

Procedure

The product from Example 45A (0.086 g, 0.75 mmol), 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-d6) 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-113e62b058894eb4b0bec2c8dba3ccc4
Source dataset
uspto-grants-2003_03
Patent number
US06538004B2

Reaction notes

Loading…