1,4-Dioxane → HCID 10404289, compound

HRID 486690Notes

Reaction equation

HRID 486690 reaction equation
[F:1][C:2]([F:26])([F:25])[C:3]1[CH:21]=[CH:20][C:6]([C:7]([C:12]([C:14]2[S:15][CH:16]=[CH:17][C:18]=2[CH3:19])=[O:13])=CN(C)C)=[C:5]([N+:22]([O-:24])=[O:23])[CH:4]=1.O1CCOCC1>O>[F:26][C:2]([F:1])([F:25])[C:3]1[CH:21]=[CH:20][C:6]([CH2:7][C:12]([C:14]2[S:15][CH:16]=[CH:17][C:18]=2[CH3:19])=[O:13])=[C:5]([N+:22]([O-:24])=[O:23])[CH:4]=1

Participants

4

Reactant 2

HCID 312751,4-DioxaneHCID 54325412HCID 54325412, compound

Product 1

HCID 10404289HCID 10404289, compoundYield 35%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A stirred solution of 6.4 g of 4-trifluoromethyl-β-(dimethylamino)-α-(3-methyl-2-thienoyl)-2-nitrostyrene, 49 ml of 1,4-dioxane, and 10 ml of water was refluxed for 42 hr. The cooled solution was concentrated, and the residue was partitioned between dichloromethane and water. The organic phase was dried over anhydrous sodium sulfate, filtered, and concentrated. The residue crystallized upon standing at room temperature. The solid was recrystallized from 95% ethanol to afford 1.9 g (35%) of product, mp 120°-122° C.

Workup

  1. concentrationThe cooled solution was concentrated
  2. customthe residue was partitioned between dichloromethane and water
  3. dry with materialThe organic phase was dried over anhydrous sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe residue crystallized
  7. customupon standing at room temperature
  8. customThe solid was recrystallized from 95% ethanol

Sources & evidence

ORD record
ord-202952b4b5794e899d636ca2b872574f
Source dataset
uspto-grants-1994_03
Patent number
US05292760

Reaction notes

Loading…