Triphenylphosphine → HCID 66651812, compound

HRID 417816Notes

Reaction equation

HRID 417816 reaction equation
[N:1]([C:4]([C:7](=[O:13])[C:8]1[CH:12]=[CH:11][S:10][CH:9]=1)([CH3:6])[CH3:5])=[N+]=[N-].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[F:33][C:34]1[CH:42]=[CH:41][CH:40]=[C:39]([F:43])[C:35]=1[C:36](Cl)=[O:37]>O.O1CCCC1.C(N(CC)CC)C>[F:33][C:34]1[CH:42]=[CH:41][CH:40]=[C:39]([F:43])[C:35]=1[C:36]([NH:1][C:4]([CH3:6])([C:7](=[O:13])[C:8]1[CH:12]=[CH:11][S:10][CH:9]=1)[CH3:5])=[O:37]

Participants

7

Reactant 3

HCID 11776TriphenylphosphineHCID 874382,6-Difluorobenzoyl chlorideHCID 23016510HCID 23016510, compound

Product 1

HCID 66651812HCID 66651812, compoundYield 74.4%

Reagents, catalysts & solvents 3

HCID 962WaterSolvent2×HCID 8028TetrahydrofuranSolvent3×HCID 8471TriethylamineSolvent

Procedure

4 ml of tetrahydrofuran and 0.08 ml of water were added to 0.68 g of 2-azido-2-(3-thenoyl)propane, then 1.10 g of triphenylphosphine was gradually added thereto with stirring at room temperature, and after completion of addition, a reaction was carried out for 18 hours. 15 ml of tetrahydrofuran was added to the reaction mixture, then 0.30 g of triethylamine was added, followed by cooling with ice, and a mixed solution of 0.46 g of 2,6-difluorobenzoyl chloride and 5 ml of tetrahydrofuran was dropwise added thereto. After completion of the dropwise addition, a reaction was carried out for 30 minutes under cooling with ice, and then a further reaction was carried out for 2.5 hours at room temperature. After completion of the reaction, the reaction mixture was put into 100 ml of water and extracted by ethyl acetate. The organic layer was dried over sodium sulfate, concentrated and purified by silica gel column chromatography (eluent: ethyl acetate/n-hexane=4/6) to obtain 0.60 g of the desired product having a melting point of from 139 to 142° C. The NMR spectrum data of this product were as follows. 1H-NMR δppm (Solvent: CDCl3/400 MHz)

Workup

  1. additionafter completion of addition
  2. temperatureby cooling with ice
  3. additionAfter completion of the dropwise addition
  4. waita reaction was carried out for 30 minutes
  5. temperatureunder cooling with ice
  6. customa further reaction
  7. waitwas carried out for 2.5 hours at room temperature
  8. customAfter completion of the reaction
  9. extractionextracted by ethyl acetate
  10. dry with materialThe organic layer was dried over sodium sulfate
  11. concentrationconcentrated
  12. custompurified by silica gel column chromatography (eluent: ethyl acetate/n-hexane=4/6)

Sources & evidence

ORD record
ord-51f4fa1ebe9a473697dcfc7e3a15c54b
Source dataset
uspto-grants-2012_01
Patent number
US08093241B2

Reaction notes

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