Phosphorus sulfide (P2S5) → HCID 13726306, compound

HRID 4825Notes

Reaction equation

HRID 4825 reaction equation
[Cl:1][CH2:2][CH2:3][CH:4]1[CH2:10][N:9]([CH3:11])[C:8](=O)[C:7]2[CH:13]=[C:14]([F:17])[CH:15]=[CH:16][C:6]=2[O:5]1.P12(SP3(SP(SP(S3)(S1)=S)(=S)S2)=S)=[S:19]>C(#N)C.C1(C)C=CC=CC=1>[Cl:1][CH2:2][CH2:3][CH:4]1[CH2:10][N:9]([CH3:11])[C:8](=[S:19])[C:7]2[CH:13]=[C:14]([F:17])[CH:15]=[CH:16][C:6]=2[O:5]1

Participants

5

Reactant 2

HCID 14817Phosphorus sulfide (P2S5)2×HCID 13726305HCID 13726305, compound

Product 1

HCID 13726306HCID 13726306, compoundYield 125.6%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 6342AcetonitrileSolvent

Procedure

To 1.0 g (0.0039 mole) of 2-(2-chloroethyl)-2,3-dihydro-7-fluoro-4-methyl-1,4-benzoxazepin-5(4H)-one in 30 ml of acetonitrile was added 0.7 g (0.0016 mole) of phosphorus pentasulfide and the reaction mixture heated to reflux. After 2 hr, another 0.4 g (0.009 mole) of phosphorus pentasulfide was added and heating continued for 2 hr. The reaction mixture was diluted with 70 ml of toluene and filtered. The filtrate was washed carefully with 3×50 ml of saturated sodium bicarbonate and 50 ml of water, dried over sodium sulfate, filtered, charcoaled, filtered and concentrated by rotary evaporation. The crude material was recrystallized from diisopropyl ether to give 0.55 g (52%) of yellow crystals, m.p. 135°-137° C.

Workup

  1. temperaturethe reaction mixture heated to reflux
  2. temperatureheating
  3. waitcontinued for 2 hr
  4. filtrationfiltered
  5. washThe filtrate was washed carefully with 3×50 ml of saturated sodium bicarbonate and 50 ml of water
  6. dry with materialdried over sodium sulfate
  7. filtrationfiltered
  8. filtrationfiltered
  9. concentrationconcentrated by rotary evaporation
  10. customThe crude material was recrystallized from diisopropyl ether

Sources & evidence

ORD record
ord-76a12ce959eb4171b4a538b09030f1f9
Source dataset
uspto-grants-1988_02
Patent number
US04727152

Reaction notes

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