1,4-Dioxane → HCID 10379793, compound

HRID 486677Notes

Reaction equation

HRID 486677 reaction equation
[Cl:1][C:2]1[CH:20]=[CH:19][C:5]([C:6]([C:11]([C:13]2[S:14][CH:15]=[CH:16][C:17]=2[CH3:18])=[O:12])=CN(C)C)=[C:4]([N+:21]([O-:23])=[O:22])[CH:3]=1.O1CCOCC1>O>[Cl:1][C:2]1[CH:20]=[CH:19][C:5]([CH2:6][C:11]([C:13]2[S:14][CH:15]=[CH:16][C:17]=2[CH3:18])=[O:12])=[C:4]([N+:21]([O-:23])=[O:22])[CH:3]=1

Participants

4

Reactant 2

HCID 312751,4-DioxaneHCID 54284844HCID 54284844, compound

Product 1

HCID 10379793HCID 10379793, compoundYield 59.9%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A stirred solution of 6.0 g of 4-chloro-β-(dimethylamino)-α-(3-methyl-2-thienoyl)-2-nitrosty rene, 50 ml of 1,4-dioxane and 10 ml of water was refluxed for 16 hr and allowed to cool. 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. A stirred solution of the residue, dioxane and water was refluxed overnight and was worked-up as above. The residue was purified by preparative HPLC (Waters Associates Prep LC/Model 500, silica gel, sample applied in dichloromethane (20 ml), eluted with dichloromethane, 200 ml/min flow rate, Gow Mac Model 80-800 UV detector). The appropriate fractions were concentrated and the residue was recrystallized from 95% ethanol to give 3.03 g of product, mp 105°-107° C.

Workup

  1. temperatureto cool
  2. concentrationThe cooled solution was concentrated
  3. customthe residue was partitioned between dichloromethane and water
  4. dry with materialThe organic phase was dried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. temperatureA stirred solution of the residue, dioxane and water was refluxed overnight
  8. customThe residue was purified by preparative HPLC (Waters Associates Prep LC/Model 500, silica gel, sample applied in dichloromethane (20 ml), eluted with dichloromethane, 200 ml/min flow rate, Gow Mac Model 80-800 UV detector)
  9. concentrationThe appropriate fractions were concentrated
  10. customthe residue was recrystallized from 95% ethanol

Sources & evidence

ORD record
ord-369324eab0b447658d4b716d53f7cb1b
Source dataset
uspto-grants-1994_03
Patent number
US05292760

Reaction notes

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