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

HRID 247276Notes

Reaction equation

HRID 247276 reaction equation
Cl.[Cl:2][CH2:3][CH2:4][CH:5]1[CH2:11][N:10]([CH3:12])[C:9](=O)[C:8]2[CH:14]=[CH:15][CH:16]=[N:17][C:7]=2[O:6]1.P12(SP3(SP(SP(S3)(S1)=S)(=S)S2)=S)=[S:19]>C(Cl)(Cl)Cl>[Cl:2][CH2:3][CH2:4][CH:5]1[CH2:11][N:10]([CH3:12])[C:9](=[S:19])[C:8]2[CH:14]=[CH:15][CH:16]=[N:17][C:7]=2[O:6]1

Participants

4

Reactant 2

HCID 14817Phosphorus sulfide (P2S5)HCID 137264372-(2-chloroethyl)-2,3-dihydro-4-methylpyrido[3,2-f][1,4]oxazepin-5(4H)one hydrochloride

Product 1

HCID 137264422-(chloroethyl)-2,3-dihydro-4-methylpyrido[3,2-f]-1,4-oxazepine-5(4H)thione

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

To a solution of 59 g (0.25 mole) of 2-(2-chloroethyl)-2,3-dihydro-4-methylpyrido[3,2-f][1,4]oxazepin-5(4H)one hydrochloride in 1500 ml of chloroform was added 41.5 g (0.19 mole) of phosphorus pentasulfide and the mixture was heated to reflux for 18 hr. The mixture was filtered and the filtrate was extracted with dilute sodium hydroxide. The chloroform layer was concentrated and the residue was dissolved in 250 ml of boiling isopropyl alcohol. On cooling, 28 g (44%) of yellow solid precipitated. A portion was recrystallized from isopropyl alcohol, m.p. 134°-136° C.

Workup

  1. temperaturethe mixture was heated
  2. temperatureto reflux for 18 hr
  3. filtrationThe mixture was filtered
  4. extractionthe filtrate was extracted with dilute sodium hydroxide
  5. concentrationThe chloroform layer was concentrated
  6. dissolutionthe residue was dissolved in 250 ml of boiling isopropyl alcohol
  7. temperatureOn cooling
  8. custom28 g (44%) of yellow solid precipitated
  9. customA portion was recrystallized from isopropyl alcohol, m.p. 134°-136° C.

Sources & evidence

ORD record
ord-435d146750a540b1bdece0ac4a839103
Source dataset
uspto-grants-1987_11
Patent number
US04705853

Reaction notes

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