Phosphorus oxychloride → HCID 10466684, compound

HRID 397047Notes

Reaction equation

HRID 397047 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH2:9][CH2:10][NH:11][C:12](=O)[C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[CH:6]=[CH:7][CH:8]=1.P(Cl)(Cl)(Cl)=O>N>[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:6](=[CH:7][CH:8]=1)[C:12]([C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)=[N:11][CH2:10][CH2:9]2

Participants

4

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 10015232HCID 10015232, compound

Product 1

HCID 10466684HCID 10466684, compoundYield 108.9%

Reagents, catalysts & solvents 1

HCID 222AmmoniaSolvent

Procedure

A solution of N-[2-(3-methoxyphenyl)ethyl]benzamide (1.530 g, 5.99 mmol) in phosphorous oxychloride (10 ml, 107.3 mmol) was refluxed under N2 for 24 hours. The cooled reaction mixture was then slowly added to ice-water (50 ml) with stirring, and basified to pH 10 with concentrated ammonia (60 ml). This was extracted with CHCl3 (4×25 ml), and the combined organic extracts were dried over MgSO4 then concentrated in vacuo to give 1.548 g (100% yield) of yellow oil.

Workup

  1. customThe cooled reaction mixture
  2. extractionThis was extracted with CHCl3 (4×25 ml)
  3. dry with materialthe combined organic extracts were dried over MgSO4
  4. concentrationthen concentrated in vacuo

Sources & evidence

ORD record
ord-c9aeb03f447949e9afb59164d4bd5a75
Source dataset
uspto-grants-2003_08
Patent number
US06608203B2

Reaction notes

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