Phosphorus sulfide (P2S5) → 2-(2-Chloroethyl)-2,3-dihydro-4-methyl-1,4-oxazepino[6,7-b]quinoline-5(4H)-thione

HRID 4820Notes

Reaction equation

HRID 4820 reaction equation
[Cl:1][CH2:2][CH2:3][CH:4]1[CH2:18][N:17]([CH3:19])[C:16](=O)[C:7]2=[N:8][C:9]3[CH:10]=[CH:11][CH:12]=[CH:13][C:14]=3[CH:15]=[C:6]2[O:5]1.P12(SP3(SP(SP(S3)(S1)=S)(=S)S2)=S)=[S:22]>C(#N)C.C1(C)C=CC=CC=1>[Cl:1][CH2:2][CH2:3][CH:4]1[CH2:18][N:17]([CH3:19])[C:16](=[S:22])[C:7]2=[N:8][C:9]3[CH:10]=[CH:11][CH:12]=[CH:13][C:14]=3[CH:15]=[C:6]2[O:5]1

Participants

5

Reactant 2

HCID 14817Phosphorus sulfide (P2S5)HCID 137263782-(2-chloroethyl)-2,3-dihydro-4-methyl-1,4-oxazepino[6,7-b]-quinolin-5(4H)-one

Product 1

HCID 137263792-(2-Chloroethyl)-2,3-dihydro-4-methyl-1,4-oxazepino[6,7-b]quinoline-5(4H)-thioneYield 86.9%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 6342AcetonitrileSolvent

Procedure

To 3.0 g (0.01 mole) of 2-(2-chloroethyl)-2,3-dihydro-4-methyl-1,4-oxazepino[6,7-b]-quinolin-5(4H)-one in 30 ml of acetonitrile was added 1.3 g (0.006 mole) of phosphorus pentasulfide. The mixture was stirred vigorously at reflux for 2 hr. After cooling, the reaction mixture was diluted with 60 ml of toluene and filtered. The residue on the filter paper was washed with 50 ml of additional toluene/acetonitrile, 3/1, V/V. The filtrate was washed with 3×50 ml saturated sodium carbonate (caution: gas evolved), dried over anhydrous sodium sulfate, filtered, treated with activated charcoal, filtered again and concentrated by rotary evaporation (90° C., 30 mm). The residual syrup was crystallized from isopropyl alcohol, yielding 1.6 g (52%) of yellow crystals, m.p. 114°-116° C.

Workup

  1. temperatureat reflux for 2 hr
  2. temperatureAfter cooling
  3. filtrationfiltered
  4. washThe residue on the filter paper was washed with 50 ml of additional toluene/acetonitrile, 3/1, V/V
  5. washThe filtrate was washed with 3×50 ml saturated sodium carbonate (caution: gas evolved)
  6. dry with materialdried over anhydrous sodium sulfate
  7. filtrationfiltered
  8. additiontreated with activated charcoal
  9. filtrationfiltered again
  10. concentrationconcentrated by rotary evaporation (90° C., 30 mm)
  11. customThe residual syrup was crystallized from isopropyl alcohol

Sources & evidence

ORD record
ord-969df2bb37174a8b86b8541a3ae806a4
Source dataset
uspto-grants-1988_02
Patent number
US04727152

Reaction notes

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