Phosphorus oxychloride → HCID 85863481, compound

HRID 2099024Notes

Reaction equation

HRID 2099024 reaction equation
[F:1][CH2:2][CH2:3][N:4]([CH3:12])[C:5]1[CH:6]=[C:7]([OH:11])[CH:8]=[CH:9][CH:10]=1.O=P(Cl)(Cl)Cl.[C:18](=O)(O)[O-:19].[Na+]>CN(C=O)C>[F:1][CH2:2][CH2:3][N:4]([CH3:12])[C:5]1[CH:10]=[CH:9][C:8]([CH:18]=[O:19])=[C:7]([OH:11])[CH:6]=1

Participants

5

Reactant 3

HCID 24813Phosphorus oxychlorideHCID 516892Sodium BicarbonateHCID 85863483HCID 85863483, compound

Product 1

HCID 85863481HCID 85863481, compoundYield 66%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

169 mg (1 mmol) 3-[(2-Fluoro-ethyl)-methyl-amino]-phenol are dissolved in 4 mL DMF and cooled below 10° C. 0.101 mL (1.1 eq.) POCl3 are added dropwise over the course of one minute, the reaction mixture is stirred 10 minutes at room temperature, then heated to 90° C. for 30 minutes. The reaction mixture is allowed to cool to 30° C. and cautiously treated with a slow addition of 8 mL saturated aqueous sodium bicarbonate solution. The desired product is extracted with ethyl acetate and saline, the organic phase dried over sodium sulfate and evaporated to yield 130 mg (66%) crude product as a slightly brownish oil. This compound is used without further purification.

Workup

  1. temperaturecooled below 10° C
  2. temperatureheated to 90° C. for 30 minutes
  3. temperatureto cool to 30° C.
  4. extractionThe desired product is extracted with ethyl acetate and saline
  5. dry with materialthe organic phase dried over sodium sulfate
  6. customevaporated

Sources & evidence

ORD record
ord-bad8014105fc4b0cabacfc1a2dbbf52d
Source dataset
uspto-grants-2009_08
Patent number
US07569337B2

Reaction notes

Loading…