Thionyl Chloride → HCID 85559966, compound

HRID 1987936Notes

Reaction equation

HRID 1987936 reaction equation
[O:1]=[C:2]1[C:15]2[CH:14]=[CH:13][C:12]([C:16]([OH:18])=O)=[CH:11][C:10]=2[O:9][C:8]2[C:3]1=[CH:4][CH:5]=[CH:6][CH:7]=2.S(Cl)([Cl:21])=O>>[O:1]=[C:2]1[C:15]2[CH:14]=[CH:13][C:12]([C:16]([Cl:21])=[O:18])=[CH:11][C:10]=2[O:9][C:8]2[C:3]1=[CH:4][CH:5]=[CH:6][CH:7]=2

Participants

3

Reactant 2

HCID 24386Thionyl ChlorideHCID 4734739-Oxo-9H-xanthene-3-carboxylic acid

Product 1

HCID 85559966HCID 85559966, compound

Procedure

9-oxo-9H-xanthene-3-carboxylic acid (9 g, 37.4 mmol) was added to thionyl chloride (28 mL, 334 mmol). The mixture was refluxed for 5 h. At that time, the thionyl chloride was removed under vacuum and the remaining residue was diluted with toluene and concentrated to dryness to give 9-oxo-9H-xanthene-3-carbonyl chloride. A portion of 9-oxo-9H-xanthene-3-carbonyl chloride (0.25 g, 0.96 mmol) was dissolved in acetonitrile (7 mL). Diisopropylethylamine (335 μL, 1.9 mmol) was then added to the mixture with the subsequent addition of pyrrolidine (113 μL, 1.3 mmol). After stirring 2 h, the solvent was concentrated and the residue was purified by reverse phase preparative HPLC, using a gradient of acetonitrile (10%- 90%) in water with trifluoroacetic acid (0.1%) to afford the 3-(pyrrolidine-1-carbonyl)-xanthen-9-one. MS m/z (MH+) 294.1.

Workup

  1. temperatureThe mixture was refluxed for 5 h
  2. customAt that time, the thionyl chloride was removed under vacuum
  3. additionthe remaining residue was diluted with toluene
  4. concentrationconcentrated to dryness

Sources & evidence

ORD record
ord-932d239c415a449d9e48bef5cd915b63
Source dataset
uspto-grants-2009_06
Patent number
US07553850B2

Reaction notes

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