Pyridine → HCID 18006811, compound

HRID 2288578Notes

Reaction equation

HRID 2288578 reaction equation
[F:1][C:2]1[CH:15]=[CH:14][C:13]2[C:4](=[C:5]([C:17]([OH:19])=O)[C:6]3[C:11]([N:12]=2)=[CH:10][CH:9]=[C:8]([F:16])[CH:7]=3)[CH:3]=1.[C:20]1(S)[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1.N1C=CC=CC=1.O=[S:34](Cl)Cl>C(Cl)Cl>[F:1][C:2]1[CH:15]=[CH:14][C:13]2[C:4](=[C:5]([C:17](=[S:34])[O:19][C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)[C:6]3[C:11]([N:12]=2)=[CH:10][CH:9]=[C:8]([F:16])[CH:7]=3)[CH:3]=1

Participants

6

Reactant 4

HCID 1049PyridineHCID 7969ThiophenolHCID 24386Thionyl ChlorideHCID 11379907HCID 11379907, compound

Product 1

HCID 18006811HCID 18006811, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

2,7-Difluoroacridine-9-carboxylic acid (1.0 g) was suspended in SOCl2 (5 mL) and the reaction mixture was refluxed for 3 h. The solvent was removed under reduced pressure leaving a brown solid which was dissolved in 20 mL of CH2Cl2 under argon. Thiophenol (468 mg) was added followed by pyridine (2 mL). The reaction mixture was stirred overnight at room temperature. The reaction mixture was diluted with CH2Cl2 and washed with water (3×50 mL). The organic layer was dried over MgSO4 and concentrated to obtain a crude material which was chromatographed on silica gel (40% ethyl acetate/hexane) to yield 1.2 g of the pure product. 1H NMR (CDCl3) δ7.52-7.75 (m, 9H), 8.26-8.30 (m, 2H).

Workup

  1. temperaturethe reaction mixture was refluxed for 3 h
  2. customThe solvent was removed under reduced pressure
  3. customleaving a brown solid which
  4. washwashed with water (3×50 mL)
  5. dry with materialThe organic layer was dried over MgSO4
  6. concentrationconcentrated
  7. customto obtain a crude material which
  8. customwas chromatographed on silica gel (40% ethyl acetate/hexane)

Sources & evidence

ORD record
ord-a05af0b6fc3a432ebd6028add485a945
Source dataset
uspto-grants-2000_07
Patent number
US06090571

Reaction notes

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