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

HRID 4804

Reaction equation

HRID 4804 reaction equation
P12(SP3(SP(SP(S3)(S1)=S)(=S)S2)=S)=S.[S-2:15].[K+].[K+].[Cl:18][CH2:19][CH2:20][CH:21]1[CH2:27][N:26]([CH3:28])[C:25](=O)[C:24]2[CH:30]=[CH:31][CH:32]=[CH:33][C:23]=2[O:22]1>C1(C)C=CC=CC=1>[Cl:18][CH2:19][CH2:20][CH:21]1[CH2:27][N:26]([CH3:28])[C:25](=[S:15])[C:24]2[CH:30]=[CH:31][CH:32]=[CH:33][C:23]=2[O:22]1

Participants

5

Reactant 3

HCID 14817Phosphorus sulfide (P2S5)HCID 162263Potassium SulfideHCID 137262932-(2-chloroethyl)-2,3-dihydro-4-methyl-1,4-benzoxazepin-5(4H)one

Product 1

HCID 137262982-(2-Chloroethyl)-2,3-dihydro-4-methyl-1,4-benzoxazepine-5(4H)-thione

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A mixture of 18.5 g (0.0834 mole) of phosphorus pentasulfide and 18.5 g potassium sulfide was ground together and added to a solution of 100 g (0.417 mole) of 2-(2-chloroethyl)-2,3-dihydro-4-methyl-1,4-benzoxazepin-5(4H)-one in dry toluene, the mixture refluxed 24 hr. and filtered. The filtrate was concentrated and partitioned between chloroform and diluted sodium hydroxide. The chloroform layer was concentrated and the residue was crystallized several times from ethanol. Yield of product was 55 g (52%), m.p. 105°-108° C.

Workup

  1. temperaturethe mixture refluxed 24 hr
  2. filtrationand filtered
  3. concentrationThe filtrate was concentrated
  4. custompartitioned between chloroform and diluted sodium hydroxide
  5. concentrationThe chloroform layer was concentrated
  6. customthe residue was crystallized several times from ethanol

Sources & evidence

ORD record
ord-8b003d3c47b34351abfb5f38c61627e5
Source dataset
uspto-grants-1988_02
Patent number
US04727152

Linked notes

Loading…