Phosphorus sulfide (P2S5) → HCID 13726304, compound

HRID 364404Notes

Reaction equation

HRID 364404 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-9c1d89479a4644349ef445528a1f5cd3
Source dataset
uspto-grants-1986_08
Patent number
US04604388

Reaction notes

Loading…