Methanol → HCID 19046233, compound

HRID 1781300Notes

Reaction equation

HRID 1781300 reaction equation
[Br:1][C:2]1[S:6][C:5]([CH:7]([NH:11][C:12](=[O:21])[C:13]2[C:18]([F:19])=[CH:17][CH:16]=[CH:15][C:14]=2[F:20])[C:8]([OH:10])=[O:9])=[CH:4][CH:3]=1.S(Cl)(Cl)=O.[CH3:26]O>>[Br:1][C:2]1[S:6][C:5]([CH:7]([NH:11][C:12](=[O:21])[C:13]2[C:14]([F:20])=[CH:15][CH:16]=[CH:17][C:18]=2[F:19])[C:8]([O:10][CH3:26])=[O:9])=[CH:4][CH:3]=1

Participants

4

Reactant 3

HCID 887MethanolHCID 24386Thionyl ChlorideHCID 19046237HCID 19046237, compound

Product 1

HCID 19046233HCID 19046233, compound

Procedure

An amount of 3.415 g (9 mmol) of the product of Step B was dissolved in 19 mL of methanol. It was cooled in an ice-bath and 1.13 mL of thionyl chloride was added dropwise. The mixture was heated at reflux for 30 min. It was cooled and the methanol removed under reduced pressure. A saturated solution of sodium bicarbonate was carefully added to the residue, then extracted with ether. The combined ether extracts were washed with brine, dried (MgSO4) and concentrated to give a white solid: mp 123°-124° C. 1H-NMR (DMSO-d6) δ9.90 (d, 1H), 7.55 (m, 1H), 7.20 (m,3H), 7.00 (d, 1H), 5.90 (d, 1H), 3.75 (s,3H).

Workup

  1. temperatureIt was cooled in an ice-bath
  2. temperatureThe mixture was heated
  3. temperatureat reflux for 30 min
  4. temperatureIt was cooled
  5. customthe methanol removed under reduced pressure
  6. additionA saturated solution of sodium bicarbonate was carefully added to the residue
  7. extractionextracted with ether
  8. washThe combined ether extracts were washed with brine
  9. dry with materialdried (MgSO4)
  10. concentrationconcentrated
  11. customto give a white solid

Sources & evidence

ORD record
ord-5bd00e53bfe843f9897be04b64fe95ed
Source dataset
uspto-grants-1997_05
Patent number
US05633271

Reaction notes

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