Phosphorus oxychloride → HCID 136334020, compound

HRID 1842729Notes

Reaction equation

HRID 1842729 reaction equation
O=P(Cl)(Cl)[Cl:3].[CH3:6][N:7]([CH3:21])/[CH:8]=[CH:9]/[C:10]([C:12]1[CH:13]=[N:14][N:15]2[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=12)=O.[F:22][P-:23]([F:28])([F:27])([F:26])([F:25])[F:24].[Na+]>C(Cl)Cl.CO>[F:22][P-:23]([F:28])([F:27])([F:26])([F:25])[F:24].[Cl:3]/[C:10](/[C:12]1[CH:13]=[N:14][N:15]2[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=12)=[CH:9]\[CH:8]=[N+:7]([CH3:21])[CH3:6]

Participants

6

Reactant 3

HCID 24813Phosphorus oxychlorideHCID 5147921Sodium hexafluorophosphateHCID 71240777HCID 71240777, compound

Product 1

HCID 136334020HCID 136334020, compoundYield 90%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

POCl3 (0.951 mL, 10.20 mmol) was added to a solution of (E)-3-(dimethylamino)-1-(pyrazolo[1,5-a]pyridin-3-yl)prop-2-en-1-one (2.153 g, 10 mmol) in CH2Cl2 (15 mL) at 20° C. (using ice/water cooling) over a period of 3 minutes under N2. The resulting solution was stirred at r.t. for 0.5 h and was then concentrated in vacuo. The residue was dissolved into a minimum amount of CH3OH (100 mL). This solution was added over a period of 2 minutes to a solution of sodium hexafluorophosphate(V) (3.36 g, 20.00 mmol) in CH3OH (40 mL). After 5 minutes the precipitate was collected by filtration, washed well with CH3OH cooled to −50° C. and dried by suction under a stream of N2 to give the title compound (3.40 g, 90%) as a yellow powder, which was used without further purification; 1H NMR: 3.63 (6H, d), 7.36 (2H, m), 7.71-7.90 (1H, m), 8.45 (1H, d), 8.81 (1H, d), 9.05 (2H, d); m/z: ES+ M+ 234.

Workup

  1. concentrationwas then concentrated in vacuo
  2. dissolutionThe residue was dissolved into a minimum amount of CH3OH (100 mL)
  3. filtrationAfter 5 minutes the precipitate was collected by filtration
  4. washwashed well with CH3OH
  5. temperaturecooled to −50° C.
  6. dry with materialdried by suction under a stream of N2

Sources & evidence

ORD record
ord-26d97b69a38e4a8fb199e706636cb3f0
Source dataset
uspto-grants-2015_02
Patent number
US08946235B2

Reaction notes

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