Phosphorus sulfide (P2S5) → 8-Chloro-2-(2-chloroethyl)-2,3-dihydro-4-methyl-1,4-benzoxazepine-5(4H)-thione

HRID 4807

Reaction equation

HRID 4807 reaction equation
[Cl:1][C:2]1[CH:17]=[CH:16][C:5]2[C:6](=O)[N:7]([CH3:14])[CH2:8][CH:9]([CH2:11][CH2:12][Cl:13])[O:10][C:4]=2[CH:3]=1.P12(SP3(SP(SP(S3)(S1)=S)(=S)S2)=S)=[S:19].[S-2].[K+].[K+]>C1(C)C=CC=CC=1>[Cl:1][C:2]1[CH:17]=[CH:16][C:5]2[C:6](=[S:19])[N:7]([CH3:14])[CH2:8][CH:9]([CH2:11][CH2:12][Cl:13])[O:10][C:4]=2[CH:3]=1

Participants

5

Reactant 3

HCID 14817Phosphorus sulfide (P2S5)HCID 162263Potassium SulfideHCID 137262948-chloro-2-(2-chloroethyl)-2,3-dihydro-4-methyl-1,4-benzoxazepin-5(4H)one

Product 1

HCID 137262998-Chloro-2-(2-chloroethyl)-2,3-dihydro-4-methyl-1,4-benzoxazepine-5(4H)-thioneYield 73.2%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a solution of 43 g (0.16 mole) of 8-chloro-2-(2-chloroethyl)-2,3-dihydro-4-methyl-1,4-benzoxazepin-5(4H)-one in 400 ml of dry toluene was added a mixture of 23 g (0.12 mole) of phosphorus pentasulfide and 23 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 to give 25.5 g (55%) of orange oil which solidified on standing at room temperature. The solid was recrystallized from ethanol, m.p. 105°-106° C.

Workup

  1. temperatureheated
  2. temperatureat reflux for 24 hr
  3. filtrationThe mixture was filtered hot
  4. concentrationthe filtrate concentrated under reduced pressure

Sources & evidence

ORD record
ord-88fc48739333487995ac8ade2e3f01a2
Source dataset
uspto-grants-1988_02
Patent number
US04727152

Linked notes

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