Phosphorus sulfide (P2S5) → HCID 13726304, compound

HRID 236167Notes

Reaction equation

HRID 236167 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]([N+:17]([O-:19])=[O:18])[CH:15]=[CH:16][C:6]=2[O:5]1.P12(SP3(SP(SP(S3)(S1)=S)(=S)S2)=S)=[S:21]>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:21])[C:7]2[CH:13]=[C:14]([N+:17]([O-:19])=[O:18])[CH:15]=[CH:16][C:6]=2[O:5]1

Participants

5

Reactant 2

HCID 14817Phosphorus sulfide (P2S5)2×HCID 137263032-(2-chloroethyl)-2,3-dihydro-4-methyl-7-nitro-1,4-benzoxazepin-5(4H)-one

Product 1

HCID 13726304HCID 13726304, compoundYield 173.5%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 6342AcetonitrileSolvent

Procedure

To 2.0 g (0.007 mole) of 2-(2-chloroethyl)-2,3-dihydro-4-methyl-7-nitro-1,4-benzoxazepin-5(4H)-one in 35 ml of acetonitrile was added 1.0 g (0.0023 mole) of phosphorus pentasulfide and the mixture heated to reflux for 2 hr. Another 0.4 g (0.001 mole) of phosphorus pentasulfide was added and heating continued for 2 hr. After cooling, 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 100 ml of water, dried over sodium sulfate, filtered, charcoaled, filtered, and concentrated by rotary evaporation. The crude oil was crystallized from isopropyl ether/toluene to give 1.2 g (57%) of yellow crystals, m.p. 153°-155° C.

Workup

  1. temperaturethe mixture heated
  2. temperatureto reflux for 2 hr
  3. temperatureheating
  4. temperatureAfter cooling
  5. filtrationfiltered
  6. washThe filtrate was washed with 3×50 ml of saturated sodium bicarbonate and 100 ml of water
  7. dry with materialdried over sodium sulfate
  8. filtrationfiltered
  9. filtrationfiltered
  10. concentrationconcentrated by rotary evaporation
  11. customThe crude oil was crystallized from isopropyl ether/toluene

Sources & evidence

ORD record
ord-5268d59f23aa4f178b2d2e90134fefe0
Source dataset
uspto-grants-1987_02
Patent number
US04642343

Reaction notes

Loading…