HCID 54483743, compound → HCID 11777428, compound

HRID 486683Notes

Reaction equation

HRID 486683 reaction equation
CN(C)C=[C:4]([C:14](=[O:21])[C:15]1[S:19][CH:18]=[CH:17][C:16]=1[CH3:20])[C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[N+:11]([O-:13])=[O:12]>O1CCOCC1.O>[N+:11]([C:6]1[CH:7]=[CH:8][CH:9]=[CH:10][C:5]=1[CH2:4][C:14]([C:15]1[S:19][CH:18]=[CH:17][C:16]=1[CH3:20])=[O:21])([O-:13])=[O:12]

Participants

4

Reactant 1

HCID 54483743HCID 54483743, compound

Product 1

HCID 11777428HCID 11777428, compoundYield 66.8%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Procedure

A solution of 62.0 g of β-(dimethylamino)-α-(3-methyl-2-thenoyl)-2-nitrostyrene in 565 ml of 1,4-dioxane and 115 ml of water was refluxed for 48 hr and concentrated. The residue was extracted with dichloromethane, and the organic phase was washed with water, dried over anhydrous sodium sulfate, filtered, and concentrated. The residue crystallized at room temperature. Recrystallization from 95% ethanol gave 34.2 g of product, mp 85°-86.5° C.

Workup

  1. concentrationconcentrated
  2. extractionThe residue was extracted with dichloromethane
  3. washthe organic phase was washed with water
  4. dry with materialdried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe residue crystallized at room temperature
  8. customRecrystallization from 95% ethanol

Sources & evidence

ORD record
ord-5d0ac589559a4d3a9e1e2e9391cb91e1
Source dataset
uspto-grants-1994_03
Patent number
US05292760

Reaction notes

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