Phosphorus oxychloride → HCID 59486210, compound

HRID 1949175Notes

Reaction equation

HRID 1949175 reaction equation
[CH2:1]([S:3][C:4]1[C:13]([C:14]([NH:16][CH2:17][C:18]2[CH:23]=[CH:22][CH:21]=[C:20]([F:24])[CH:19]=2)=[O:15])=[C:12](O)[C:11]2[C:6](=[CH:7][C:8]([C:26]([F:29])([F:28])[F:27])=[CH:9][CH:10]=2)[N:5]=1)[CH3:2].O=P(Cl)(Cl)[Cl:32].C([O-])(O)=O.[Na+]>CCCCCC>[Cl:32][C:12]1[C:11]2[C:6](=[CH:7][C:8]([C:26]([F:29])([F:28])[F:27])=[CH:9][CH:10]=2)[N:5]=[C:4]([S:3][CH2:1][CH3:2])[C:13]=1[C:14]([NH:16][CH2:17][C:18]1[CH:23]=[CH:22][CH:21]=[C:20]([F:24])[CH:19]=1)=[O:15]

Participants

5

Reactant 3

HCID 24813Phosphorus oxychlorideHCID 516892Sodium BicarbonateHCID 178477332HCID 178477332, compound

Product 1

HCID 59486210HCID 59486210, compoundYield 48%

Reagents, catalysts & solvents 1

HCID 8058HexaneSolvent

Conditions

Temperature
130 °C

Procedure

A mixture of 1.0 g (2.36 mmol) 2-(ethylthio)-N-(3-fluorobenzyl)-4-hydroxy-7-(trifluoromethyl)quinoline-3-carboxamide and POCl3 (10 ml) was heated for 2 h at 130° C. After cooling to RT the mixture was adjusted to pH ˜8 with a saturated aqueous NaHCO3 solution and extracted with EE. The organic phase was washed with water and brine, dried over Na2SO4, filtered and concentrated to small volume under vacuum. Column chromatography (hexane/EE 22:3) of the residue yielded 0.5 g (1.1 mmol, 48%) 4-chloro-2-ethylsulfanyl-N-[(3-fluorophenyl)-methyl]-7-(trifluoromethyl)-quinoline-3-carboxamide. MS: m/z 443.1 [M+H]+.

Workup

  1. temperatureAfter cooling to RT the mixture
  2. extractionextracted with EE
  3. washThe organic phase was washed with water and brine
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated to small volume under vacuum

Sources & evidence

ORD record
ord-a9594b1c1dcd406685693cb78d55566e
Source dataset
uspto-grants-2013_03
Patent number
US08399673B2

Reaction notes

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