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

HRID 247275

Reaction equation

HRID 247275 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 dilute 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 dilute sodium hydroxide
  5. concentrationThe chloroform layer was concentrated
  6. customthe residue was crystallized several times from ethanol

Sources & evidence

ORD record
ord-865f8467d8514014988eff3672c66983
Source dataset
uspto-grants-1987_11
Patent number
US04705853

Linked notes

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