Phosphorus sulfide (P2S5) → HCID 13726304, compound

HRID 247297Notes

Reaction equation

HRID 247297 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-e09f894afa8c44ec9acfd49ec21fc808
Source dataset
uspto-grants-1987_11
Patent number
US04705853

Reaction notes

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