Ethyl Acetate → HCID 15680010, compound

HRID 359881Notes

Reaction equation

HRID 359881 reaction equation
[CH3:1][N+:2]1[CH:7]=[CH:6][CH:5]=[C:4]([C:8](=[O:35])[NH:9][CH:10]2[CH2:15][CH2:14][CH:13]([O:16][C:17](=[O:34])[CH2:18][CH2:19][CH2:20][C:21]3[CH:26]=[CH:25][C:24]([N:27]([CH2:31][CH2:32][Cl:33])[CH2:28][CH2:29][Cl:30])=[CH:23][CH:22]=3)[CH2:12][CH2:11]2)[CH:3]=1.C(=O)(O)[O-].[Na+].S(S([O-])=O)([O-])=O.[Na+].[Na+].C(OCC)(=O)C>C(#N)C.O>[CH3:1][N:2]1[CH:7]=[CH:6][CH2:5][C:4]([C:8](=[O:35])[NH:9][CH:10]2[CH2:15][CH2:14][CH:13]([O:16][C:17](=[O:34])[CH2:18][CH2:19][CH2:20][C:21]3[CH:22]=[CH:23][C:24]([N:27]([CH2:31][CH2:32][Cl:33])[CH2:28][CH2:29][Cl:30])=[CH:25][CH:26]=3)[CH2:12][CH2:11]2)=[CH:3]1

Participants

7

Reactant 4

HCID 8857Ethyl AcetateHCID 24489Sodium DithioniteHCID 516892Sodium BicarbonateHCID 15680009HCID 15680009, compound

Product 1

HCID 15680010HCID 15680010, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6342AcetonitrileSolvent

Conditions

Temperature
0 °C

Procedure

The quaternary salt prepared in Example 81 (0.34 g, 05 mol) was dissolved in 0.5 mL of acetonitrile and taken up in 20 mL of degassed water (bubbling N2) cooled to 0° C. To the stirring solution, sodium bicarbonate (0.27 g, 0.003 mol) was added, followed first by 0.37 g (0.002 mol) of sodium dithionite and then by 20 mL of ethyl acetate. After 90 minutes, the organic phase was removed and the aqueous phase was extracted 3 to 4 times with ethyl acetate. The ethyl acetate extracts were combined, dried over sodium sulfate and evaporated in vacuo. The residual solid was washed several times with anhydrous ether and dried. The residue thus obtained was applied to a neutral alumina column and eluted with chloroform under pressure. Evaporation of chloroform left 0.18 g (65%) of a hygroscopic yellow solid of the formula ##STR116## The identity of the product was confirmed by UV analysis.

Workup

  1. customthe organic phase was removed
  2. extractionthe aqueous phase was extracted 3 to 4 times with ethyl acetate
  3. dry with materialdried over sodium sulfate
  4. customevaporated in vacuo
  5. washThe residual solid was washed several times with anhydrous ether
  6. customdried
  7. customThe residue thus obtained
  8. washeluted with chloroform under pressure
  9. customEvaporation of chloroform
  10. waitleft 0.18 g (65%) of a hygroscopic yellow solid of the formula ##STR116## The identity of the product

Sources & evidence

ORD record
ord-428fd32410df4cacaa6dbf194faa84bb
Source dataset
uspto-grants-1991_03
Patent number
US05002935

Reaction notes

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