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

HRID 1193791Notes

Reaction equation

HRID 1193791 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-0dbc9157fe2c4cafa47bcbb678872355
Source dataset
uspto-grants-1989_03
Patent number
US04810795

Reaction notes

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