Phosphorus sulfide (P2S5) → HCID 13726452, compound

HRID 247295Notes

Reaction equation

HRID 247295 reaction equation
[Br:1][C:2]1[CH:12]=[N:11][C:10]2[O:9][CH:8]([CH2:13][CH2:14][Cl:15])[CH2:7][N:6]([CH3:16])[C:5](=O)[C:4]=2[CH:3]=1.P12(SP3(SP(SP(S3)(S1)=S)(=S)S2)=S)=[S:19]>C(#N)C.C1(C)C=CC=CC=1>[Br:1][C:2]1[CH:12]=[N:11][C:10]2[O:9][CH:8]([CH2:13][CH2:14][Cl:15])[CH2:7][N:6]([CH3:16])[C:5](=[S:19])[C:4]=2[CH:3]=1

Participants

5

Reactant 2

HCID 14817Phosphorus sulfide (P2S5)HCID 13726451HCID 13726451, compound

Product 1

HCID 13726452HCID 13726452, compoundYield 59.6%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 6342AcetonitrileSolvent

Procedure

To a solution of 5.9 g (0.016 mole) of 7-bromo-2-(2-chloroethyl)-2,3-dihydro-4-methylpyrido[3,2-f]-1,4-oxazepin-5(4H)-one in 25 ml of acetonitrile was added 2.07 g (0.005 mole) of phosphorus pentasulfide. The mixture was heated to reflux for 3 hr. The reaction mixture was diluted with 100 ml of toluene and filtered. The filtrate was washed with 3×50 ml of saturated sodium bicarbonate and 50 ml of water, dried over sodium sulfate, filtered, and concentrated by rotary evaporation to ~5-10 ml. Crystallization ensued and 3.0 g of crystals were collected. The mother liquor was concentrated giving 1.0 g additional crystals. The two crops were combined and recrystallized from diisopropylether/toluene to give ~3 g (56%) of yellow crystals, m.p. 138°-141° C.

Workup

  1. temperatureThe mixture was heated
  2. temperatureto reflux for 3 hr
  3. filtrationfiltered
  4. washThe filtrate was washed with 3×50 ml of saturated sodium bicarbonate and 50 ml of water
  5. dry with materialdried over sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated by rotary evaporation to ~5-10 ml
  8. customCrystallization
  9. custom3.0 g of crystals were collected
  10. concentrationThe mother liquor was concentrated

Sources & evidence

ORD record
ord-741f91f44ebe47dc99c7d194ee5c3df8
Source dataset
uspto-grants-1987_11
Patent number
US04705853

Reaction notes

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