Phosphorus oxychloride → HCID 86691864, compound

HRID 517693Notes

Reaction equation

HRID 517693 reaction equation
[CH3:1][N:2]([CH3:17])[CH:3]=[CH:4][C:5]([C:7]1[CH:12]=[CH:11][C:10]([C:13]([F:16])([F:15])[F:14])=[CH:9][CH:8]=1)=O.O=P(Cl)(Cl)[Cl:20].[Cl:23]([O-:27])(=[O:26])(=[O:25])=[O:24].[Na+]>ClCCl.O.C(OCC)C>[Cl:23]([O-:27])(=[O:26])(=[O:25])=[O:24].[Cl:20][C:5]([C:7]1[CH:12]=[CH:11][C:10]([C:13]([F:16])([F:15])[F:14])=[CH:9][CH:8]=1)=[CH:4][CH:3]=[N+:2]([CH3:17])[CH3:1]

Participants

7

Reactant 3

HCID 24813Phosphorus oxychlorideHCID 522606Sodium PerchlorateHCID 2805938HCID 2805938, compound2×

Product 1

HCID 86691864HCID 86691864, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolvent

Procedure

A solution of 3-(dimethylamino)-1-[4-(trifluoromethyl)phenyl]-2-propen-1-one (may be prepared as described in Intermediate 2) (1.49 g, 6.13 mmol) in dichloromethane (DCM) (6 ml) was cooled in an ice-water bath before the dropwise addition of POCl3 (0.571 ml, 6.13 mmol). The ice-water bath was removed and the reaction mixture stirred at room temperature for 3 hours. The solvent was removed under vacuum to yield a solid. To the solid was then added to an ice-cold solution of sodium perchlorate (3.75 g, 30.6 mmol) in water (8 mL) and diethyl ether (2 mL). The resulting suspension was stirred in an ice-water bath for 20 minutes. The solid was then collected by filtration, washed with ice-cold water (4 mL), dried by suction for 40 minutes then dried overnight under vacuum to yield the title compound as a solid (2.39 g.

Workup

  1. customThe ice-water bath was removed
  2. customThe solvent was removed under vacuum
  3. customto yield a solid
  4. stirringThe resulting suspension was stirred in an ice-water bath for 20 minutes
  5. filtrationThe solid was then collected by filtration
  6. washwashed with ice-cold water (4 mL)
  7. customdried by suction for 40 minutes
  8. customthen dried overnight under vacuum

Sources & evidence

ORD record
ord-745fe590736941438347c175c764ff78
Source dataset
uspto-grants-2015_08
Patent number
US09115132B2

Reaction notes

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