1,4-Dioxane → HCID 10404289, compound

HRID 1721345Notes

Reaction equation

HRID 1721345 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-13df8be8f96e4c12b4166f1b77677943
Source dataset
uspto-grants-1996_04
Patent number
US05510346

Reaction notes

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