Phosphorus oxychloride → HCID 15586693, compound

HRID 255698Notes

Reaction equation

HRID 255698 reaction equation
[CH3:1][N:2]([CH3:29])[CH2:3][CH2:4][CH2:5][N:6]([C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)[C:7]1[C:12]([NH:13][C:14](=O)[C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=2[F:21])=[CH:11][CH:10]=[CH:9][N:8]=1.P(Cl)(Cl)(Cl)=O>O>[F:21][C:16]1[CH:17]=[CH:18][CH:19]=[CH:20][C:15]=1[C:14]1[C:24]2[CH:25]=[CH:26][CH:27]=[CH:28][C:23]=2[N:6]([CH2:5][CH2:4][CH2:3][N:2]([CH3:29])[CH3:1])[C:7]2[N:8]=[CH:9][CH:10]=[CH:11][C:12]=2[N:13]=1

Participants

4

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 13560177HCID 13560177, compound

Product 1

HCID 15586693HCID 15586693, compoundYield 39%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A solution of 8.5 g (0.022 mole) of N-[2-[[3-(dimethylamino)propyl]phenylamino]-3-pyridinyl]-2-fluorobenzamide in 26 g (0.173 mole) of phosphorus oxychloride was refluxed under nitrogen atmosphere for 16 hr. The cooled reaction mixture was poured over ice, diluted with water, and extracted twice with diethyl ether. The acidic portion was made basic with sodium hydroxide pellets, cooled with ice and extracted twice with methylene chloride. The combined methylene chloride layers were washed in sequence with water and saturated sodium chloride, dried over sodium sulfate and concentrated in vacuo. The residue was crystallized from isopropyl alcohol-isopropyl ether using charcoal treatment to yield 3.2 g (39%) of a bright-yellow solid, m.p. 92°-94° C.

Workup

  1. customThe cooled reaction mixture
  2. additionwas poured over ice
  3. extractionextracted twice with diethyl ether
  4. temperaturecooled with ice
  5. extractionextracted twice with methylene chloride
  6. washThe combined methylene chloride layers were washed in sequence with water and saturated sodium chloride
  7. dry with materialdried over sodium sulfate
  8. concentrationconcentrated in vacuo
  9. customThe residue was crystallized from isopropyl alcohol-isopropyl ether

Sources & evidence

ORD record
ord-34b1e40819b24493a2275ba03a435b2a
Source dataset
uspto-grants-1987_10
Patent number
US04698430

Reaction notes

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