Phosphorus pentachloride → 2-(4-chloro-2-fluoro-5-propargyloxyphenylimino)-2-(pyrrolidine-1-yl)acetaldehyde O-methyloxime

HRID 1510927Notes

Reaction equation

HRID 1510927 reaction equation
[Cl:1][C:2]1[C:7]([O:8][CH2:9][C:10]#[CH:11])=[CH:6][C:5]([NH:12][C:13](=O)[CH:14]=[N:15][O:16][CH3:17])=[C:4]([F:19])[CH:3]=1.P(Cl)(Cl)(Cl)(Cl)Cl.[NH:26]1[CH2:30][CH2:29][CH2:28][CH2:27]1>C1C=CC=CC=1.ClCCl>[CH3:17][O:16][N:15]=[CH:14][C:13](=[N:12][C:5]1[CH:6]=[C:7]([O:8][CH2:9][C:10]#[CH:11])[C:2]([Cl:1])=[CH:3][C:4]=1[F:19])[N:26]1[CH2:30][CH2:29][CH2:28][CH2:27]1

Participants

6

Reactant 3

HCID 24819Phosphorus pentachlorideHCID 31268PyrrolidineHCID 86660105N-(4-chloro-2-fluoro-5-propargyloxyphenyl)-2-(methoxyimino)acetamide

Product 1

HCID 866601062-(4-chloro-2-fluoro-5-propargyloxyphenylimino)-2-(pyrrolidine-1-yl)acetaldehyde O-methyloximeYield 64.2%

Reagents, catalysts & solvents 2

HCID 241BenzeneSolventHCID 6344DichloromethaneSolvent

Procedure

0.42 g of the obtained N-(4-chloro-2-fluoro-5-propargyloxyphenyl)-2-(methoxyimino)acetamide was dissolved in 30 ml of benzene and after the addition of 0.36 g of phosphorus pentachloride, the resulting solution was refluxed for 4 hours. The concentrate obtained by concentrating the resulting reaction solution under reduced pressure was dissolved in 20 ml of dichloromethane and 0.32 g of pyrrolidine was added dropwise thereto at room temperature and the resultant solution was stirred at room temperature for 1 hour. The concentrate obtained by evaporating solvents from the resulting reaction solution under reduced pressure was purified by silica gel column chromatography to obtain 0.32 g of 2-(4-chloro-2-fluoro-5-propargyloxyphenylimino)-2-(pyrrolidine-1-yl)acetaldehyde O-methyloxime (1-5) (yield 64%). m.p. 73-75° C.

Workup

  1. temperaturethe resulting solution was refluxed for 4 hours
  2. customThe concentrate obtained
  3. concentrationby concentrating
  4. customthe resulting reaction solution under reduced pressure
  5. customThe concentrate obtained
  6. customby evaporating solvents
  7. customfrom the resulting reaction solution under reduced pressure
  8. customwas purified by silica gel column chromatography

Sources & evidence

ORD record
ord-a370d7d2ea5747e1972861d96141190f
Source dataset
uspto-grants-2012_07
Patent number
US08212050B2

Reaction notes

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