Phosphorus sulfide (P2S5) → 7-Bromo-2-(2-chloroethyl)-2,3-dihydro-4-methyl-1,4-benzoxazepine-5(4H)-thione

HRID 4808

Reaktionsgleichung

Reaktionsgleichung von HRID 4808
[Br:1][C:2]1[CH:3]=[CH:4][C:5]2[O:11][CH:10]([CH2:12][CH2:13][Cl:14])[CH2:9][N:8]([CH3:15])[C:7](=O)[C:6]=2[CH:17]=1.P12(SP3(SP(SP(S3)(S1)=S)(=S)S2)=S)=[S:19].[S-2].[K+].[K+]>C1(C)C=CC=CC=1>[Br:1][C:2]1[CH:3]=[CH:4][C:5]2[O:11][CH:10]([CH2:12][CH2:13][Cl:14])[CH2:9][N:8]([CH3:15])[C:7](=[S:19])[C:6]=2[CH:17]=1

Komponenten

5

Edukt 3

HCID 14817Phosphorus sulfide (P2S5)HCID 162263Potassium SulfideHCID 137262957-bromo-2-(2-chloroethyl)-2,3-dihydro-4-methyl-1,4-benzoxazepin-5(4H)one

Produkt 1

HCID 137263007-Bromo-2-(2-chloroethyl)-2,3-dihydro-4-methyl-1,4-benzoxazepine-5(4H)-thioneAusbeute 72,6 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1140TolueneLösungsmittel

Versuchsvorschrift

To a solution of 11.0 g (0.035 mole) of 7-bromo-2-(2-chloroethyl)-2,3-dihydro-4-methyl-1,4-benzoxazepin-5(4H)-one in 150 ml of dry toluene was added a mixture of 13.4 g (0.07 mole) of phosphorus pentasulfide and 13.4 g of potassium sulfide which had been ground together. The reaction mixture was heated at reflux for 5 hr under a nitrogen atmosphere. The mixture was filtered hot and the filtrate concentrated under reduced pressure. The residue was dissolved in chloroform. The chloroform solution was washed twice with dilute aqueous sodium hydroxide, dried over magnesium sulfate and concentrated under reduced pressure to give 8.5 g (72%) of yellow solid. The solid was recrystallized from ethanol, m.p. 118°-120° C.

Aufarbeitung

  1. temperatureThe reaction mixture was heated
  2. temperatureat reflux for 5 hr under a nitrogen atmosphere
  3. filtrationThe mixture was filtered hot
  4. concentrationthe filtrate concentrated under reduced pressure
  5. dissolutionThe residue was dissolved in chloroform
  6. washThe chloroform solution was washed twice with dilute aqueous sodium hydroxide
  7. dry with materialdried over magnesium sulfate
  8. concentrationconcentrated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-bf2c4a25c1be4e5398f1ee32fffc150d
Quelldatensatz
uspto-grants-1988_02
Patentnummer
US04727152

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