Phosphorus sulfide (P2S5) → 2-(2-Chloroethyl)-2,3-dihydro-4-methylnaphth[2,3-f][1,4]oxazepine-5(4H)-thione

HRID 247277Notes

Reaction equation

HRID 247277 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]3[C:19](=[CH:20][C:6]=2[O:5]1)[CH:18]=[CH:17][CH:16]=[CH:15]3.P12(SP3(SP(SP(S3)(S1)=S)(=S)S2)=S)=[S:22].[S-2].[K+].[K+]>C1(C)C=CC=CC=1>[Cl:1][CH2:2][CH2:3][CH:4]1[CH2:10][N:9]([CH3:11])[C:8](=[S:22])[C:7]2[CH:13]=[C:14]3[C:19](=[CH:20][C:6]=2[O:5]1)[CH:18]=[CH:17][CH:16]=[CH:15]3

Participants

5

Reactant 3

HCID 14817Phosphorus sulfide (P2S5)HCID 162263Potassium SulfideHCID 137263632-(2-chloroethyl)-2,3-dihydro-4-methylnaphth[2,3-f][1,4]oxazepin-5(4H)-one

Product 1

HCID 137263642-(2-Chloroethyl)-2,3-dihydro-4-methylnaphth[2,3-f][1,4]oxazepine-5(4H)-thione

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a solution of 16.6 g (0.06 mole) of 2-(2-chloroethyl)-2,3-dihydro-4-methylnaphth[2,3-f][1,4]oxazepin-5(4H)-one in 150 ml of dry toluene was added a mixture of 8.6 g (0.045 mole) of phosphorus pentasulfide and 8.6 g of potassium sulfide which had been ground together. The reaction mixture was stirred and heated at reflux for 24 hr. The mixture was filtered hot and the filtrate concentrated under reduced pressure. Yellow solid, 6.5 g (35%) was obtained which was recrystallized from ethanol, m.p. 166°-168° C.

Workup

  1. temperatureheated
  2. temperatureat reflux for 24 hr
  3. filtrationThe mixture was filtered hot
  4. concentrationthe filtrate concentrated under reduced pressure
  5. customYellow solid, 6.5 g (35%) was obtained which
  6. customwas recrystallized from ethanol, m.p. 166°-168° C.

Sources & evidence

ORD record
ord-9a395094c2e740439167821dc4da8008
Source dataset
uspto-grants-1987_11
Patent number
US04705853

Reaction notes

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