HCID 18184523, compound → HCID 10311354, compound

HRID 1358475Notes

Reaction equation

HRID 1358475 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH2:11][C:12]([NH:14][CH2:15][CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[C:19]([NH:23][S:24]([CH3:27])(=[O:26])=[O:25])[CH:18]=2)=O)[CH:5]=[C:6]([Br:10])[C:7]=1[O:8][CH3:9]>C(#N)C.P(Cl)(Cl)(Cl)=O>[Br:1][C:2]1[CH:3]=[C:4]([CH:5]=[C:6]([Br:10])[C:7]=1[O:8][CH3:9])[CH2:11][CH:12]1[C:22]2[C:17](=[CH:18][C:19]([NH:23][S:24]([CH3:27])(=[O:26])=[O:25])=[CH:20][CH:21]=2)[CH2:16][CH2:15][NH:14]1

Participants

4

Reactant 1

HCID 18184523HCID 18184523, compound

Product 1

HCID 10311354HCID 10311354, compound

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 24813Phosphorus oxychlorideSolvent

Procedure

To solution of 2-(3,5-dibromo-4-methoxy-phenyl)-N-[2-(3-methanesulfonylamino-phenyl)-ethyl]-acetamide in 15 mL of acetonitrile, phosphorus oxychloride is added. The reaction mixture is refluxed for 5 h. The residue after concentration is evaporated 3 times with MeOH, dissolved in 20 mL of MeOH, cooled with an ice bath, and NaBH4 is added by small portions. The reaction mixture is stirred overnight at room temperature, concentrated, dissolved in chloroform, washed with 1N NaOH, dried over Na2SO4, filtered, and concentrated. The residue is dissolved in methanol, and a solution of (COOH)2.2H2O in methanol is added.

Workup

  1. temperatureThe reaction mixture is refluxed for 5 h
  2. concentrationThe residue after concentration
  3. customis evaporated 3 times with MeOH
  4. dissolutiondissolved in 20 mL of MeOH
  5. temperaturecooled with an ice bath
  6. additionNaBH4 is added by small portions
  7. concentrationconcentrated
  8. dissolutiondissolved in chloroform
  9. washwashed with 1N NaOH
  10. dry with materialdried over Na2SO4
  11. filtrationfiltered
  12. concentrationconcentrated
  13. dissolutionThe residue is dissolved in methanol
  14. addition2H2O in methanol is added

Sources & evidence

ORD record
ord-1d414d1b67814b9282ae4703b810588c
Source dataset
uspto-grants-2003_07
Patent number
US06596734B1

Reaction notes

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