Phosphorus pentachloride → HCID 21315972, compound

HRID 614220Notes

Reaction equation

HRID 614220 reaction equation
[Cl:1][C:2]1[S:3][CH:4]=[C:5]2[C:11](=O)[NH:10][C:9]3[CH:13]=[CH:14][CH:15]=[CH:16][C:8]=3[O:7][C:6]=12.P(Cl)(Cl)(Cl)(Cl)[Cl:18]>C1(C)C=CC=CC=1>[Cl:1][C:2]1[S:3][CH:4]=[C:5]2[C:11]([Cl:18])=[N:10][C:9]3[CH:13]=[CH:14][CH:15]=[CH:16][C:8]=3[O:7][C:6]=12

Participants

4

Reactant 2

HCID 24819Phosphorus pentachlorideHCID 12581868HCID 12581868, compound

Product 1

HCID 21315972HCID 21315972, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A 4.0 g. portion of 3-chlorothieno[3,4-b][1,5]benzoxazepin-10(9H)-one (Example 12) and 4.0 g. of phosphorus pentachloride in 103 ml. of dry toluene is refluxed for 41/2 hours. The reaction temperature is concentrated, then is triturated with toluene to give 3,10-dichlorothieno[3,4-b][1,5]benzoxazepine. A 25 ml. amount of dry N-(2-hydroxyethyl)piperazine and 25 ml of dry toluene is added to the product above and the mixture is heated at 120° C. for 16 hours. The reaction mixture is concentrated to a thick oil, the oil is dissolved in hot 2N aqueous acetic acid, treated with activated charcoal and filtered through diatomaceous earth. The filtrate is cooled and precipitated with concentrated ammonium hydroxide. The precipitate is collected and extracted into methylene chloride, the organic solution is dried over anhydrous sodium sulfate and eluted through magnesium silicate with 2.5 liters of methylene chloride followed by one liter of 1:1 ethyl acetate:methylene chloride. The combined organic solvents are evaporated to yield 2.0 g. of 4-(3-chlorothieno[3,4-b][1,5]-benzoxazepin-10-yl)-1-piperazineethanol.

Workup

  1. concentrationThe reaction temperature is concentrated
  2. customis triturated with toluene

Sources & evidence

ORD record
ord-8112c367432b4dc09c10f93c85138da9
Source dataset
uspto-grants-1979_03
Patent number
US04144235

Reaction notes

Loading…