Phosphorus oxychloride → HCID 59198477, compound

HRID 1896525Notes

Reaction equation

HRID 1896525 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]2[C:8]3[C:9](=O)[NH:10][CH:11]=[C:12]([C:15]([NH2:17])=O)[C:13]=3[S:14][C:4]=2[CH:3]=1.O=P(Cl)(Cl)[Cl:21].C([O-])(O)=O.[Na+]>CCOC(C)=O>[Br:1][C:2]1[CH:7]=[CH:6][C:5]2[C:8]3[C:9]([Cl:21])=[N:10][CH:11]=[C:12]([C:15]#[N:17])[C:13]=3[S:14][C:4]=2[CH:3]=1

Participants

5

Reactant 3

HCID 24813Phosphorus oxychlorideHCID 516892Sodium BicarbonateHCID 591984567-Bromo-1-oxo-1,2-dihydro[1]benzothieno[3,2-c]pyridine-4-carboxamide

Product 1

HCID 59198477HCID 59198477, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 7-bromo-1-oxo-1,2-dihydro[1]benzothieno[3,2-c]pyridine-4-carboxamide and POCl3 (29 equiv) was heated to refluxed for 8 h. The mixture was poured onto ice, neutralized with NaHCO3, filtered, washed with H2O and dried to give a yellow solid. The crude product was heated to reflux with 20% EtOAc in hexanes, cooled and filtered to give the title compound.

Workup

  1. temperaturewas heated
  2. temperatureto refluxed for 8 h
  3. additionThe mixture was poured onto ice
  4. filtrationfiltered
  5. washwashed with H2O
  6. customdried
  7. customto give a yellow solid
  8. temperaturecooled
  9. filtrationfiltered

Sources & evidence

ORD record
ord-979d39e5a39a4ba7bbf17e1bc4f3c0b8
Source dataset
uspto-grants-2013_08
Patent number
US08518964B2

Reaction notes

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