Phosphorus oxychloride → HCID 178438029, compound

HRID 921523Notes

Reaction equation

HRID 921523 reaction equation
P(Cl)(Cl)([Cl:3])=O.[CH2:6]([C:8]1[C:16]2[C:11](=[N+:12]([O-])[CH:13]=[CH:14][CH:15]=2)[NH:10][N:9]=1)[CH3:7]>ClC(Cl)C>[Cl:3][C:15]1[CH:14]=[CH:13][N:12]=[C:11]2[NH:10][N:9]=[C:8]([CH2:6][CH3:7])[C:16]=12

Participants

4

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 178437981HCID 178437981, compound

Product 1

HCID 178438029HCID 178438029, compoundYield 47%

Reagents, catalysts & solvents 1

HCID 63651,1-DichloroethaneSolvent

Procedure

Phosphorus oxychloride (11.1 mL) was added to a suspension solution of compound (3b) (19.5 g) in dichloroethane (240 mL) at room temperature, followed by stirring for 30 min. The solvent of the reaction solution was distilled away, and then acetonitrile (40 mL), methanol (40 mL), and water (80 mL) were added to the residue. After adjustment of pH to 9 with an aqueous sodium hydroxide solution, water (400 mL) was added thereto. The precipitate was collected by filtration, washed by sprinkling methanol (40 mL), water (300 mL), ether (60 mL), and hexane (30 mL), sequentially, and dried under reduced pressure to obtain compound (3c) (10.2 g, 47%) as a white solid.

Workup

  1. distillationThe solvent of the reaction solution was distilled away
  2. additionacetonitrile (40 mL), methanol (40 mL), and water (80 mL) were added to the residue
  3. additionwas added
  4. filtrationThe precipitate was collected by filtration
  5. washwashed
  6. customsequentially, and dried under reduced pressure

Sources & evidence

ORD record
ord-1e7cd04c2c6e468c87fb0f22f6b0c0d8
Source dataset
uspto-grants-2016_03
Patent number
US09273045B2

Reaction notes

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