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

HRID 247282Notes

Reaction equation

HRID 247282 reaction equation
[Cl:1][CH2:2][CH2:3][CH:4]1[CH2:10][N:9]([CH3:11])[C:8](=O)[C:7]2[CH:13]=[C:14]([O:17][CH3:18])[CH:15]=[CH:16][C:6]=2[O:5]1.P12(SP3(SP(SP(S3)(S1)=S)(=S)S2)=S)=[S:20].[S-2].[K+].[K+]>C(Cl)(Cl)Cl>[Cl:1][CH2:2][CH2:3][CH:4]1[CH2:10][N:9]([CH3:11])[C:8](=[S:20])[C:7]2[CH:13]=[C:14]([O:17][CH3:18])[CH:15]=[CH:16][C:6]=2[O:5]1

Participants

5

Reactant 3

HCID 14817Phosphorus sulfide (P2S5)HCID 162263Potassium SulfideHCID 137262972-(2-Chloroethyl)-2,3-dihydro-7-methoxy-4-methyl-1,4-benzoxazepin-5(4H)-one

Product 1

HCID 137263022-(2-Chloroethyl)-2,3-dihydro-7-methoxy-4-methyl-1,4-benzoxazepine-5(4H)-thioneYield 86.3%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

To a solution of 10.3 g (0.04 mole) of 2-(2-chloroethyl)-2,3-dihydro-7-methoxy-4-methyl-1,4-benzoxazepin-5(4H)-one in 200 ml of chloroform was added a mixture of 5.7 g (0.03 mole) of phosphorus pentasulfide and 5.7 g of potassium sulfide which had been ground together. The reaction mixture was stirred and heated at reflux under nitrogen atmosphere for 5 hr. The mixture was filtered hot and the filtrate concentrated under reduced pressure. The residue, an orange solid, was recrystallized from ethanol to give 7.4 g (65%) of product, m.p. 98°-100° C.

Workup

  1. temperatureheated
  2. temperatureat reflux under nitrogen atmosphere for 5 hr
  3. filtrationThe mixture was filtered hot
  4. concentrationthe filtrate concentrated under reduced pressure
  5. customThe residue, an orange solid, was recrystallized from ethanol

Sources & evidence

ORD record
ord-9316269126f749ad8e614ee45c94ff5f
Source dataset
uspto-grants-1987_11
Patent number
US04705853

Reaction notes

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